Utilizing biocatalysis and a sulfolane-mediated reductive acetal opening to access nemtabrutinib from cyrene
The chiral building block 5-amino-2-hydroxymethyltetrahydropyran 1a has been previously synthesized through a cumbersome 9-step synthesis from tri- O -acetyl-D-glucal, which renders access to nemtabrutinib ( 2 ), a BTK inhibitor currently being evaluated for the treatment of various hematologic mali...
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Published in | Green chemistry : an international journal and green chemistry resource : GC Vol. 25; no. 2; pp. 66 - 613 |
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Main Authors | , , , , , , , , , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Cambridge
Royal Society of Chemistry
23.01.2023
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Abstract | The chiral building block 5-amino-2-hydroxymethyltetrahydropyran
1a
has been previously synthesized through a cumbersome 9-step synthesis from tri-
O
-acetyl-D-glucal, which renders access to nemtabrutinib (
2
), a BTK inhibitor currently being evaluated for the treatment of various hematologic malignancies, inefficient and wasteful. Herein, we describe the development of a protecting group-free, 2-step synthesis of
1a
from Cyrene™, a biorenewable feedstock. The improved synthesis involves a biocatalytic transamination reaction of Cyrene™ to install the desired amine stereocenter in a single step with high diastereoselectivity. The enzymatic reaction is followed by a stereo-retentive reductive acetal opening reaction of the chiral cyrene amine intermediate
3a
to furnish
1a
. A mechanistic investigation of the acetal opening reaction is also described which uncovered reaction conditions for the sulfolane mediated
in situ
generation of diborane as the active reductant. The streamlined synthesis of
1a
from Cyrene™ reduced the step count from 9 to 2 synthetic steps which resulted in a >27% yield improvement and a significant reduction in the environmental impact of the synthesis.
The development of a protecting group-free, 2-step synthesis of 5-amino-2-hydroxymethyltetrahydropyran
1a
from biorenewable Cyrene™ is described which renders access to BTK-inhibitor nemtabrutinib (
2
) more efficient and sustainable. |
---|---|
AbstractList | The chiral building block 5-amino-2-hydroxymethyltetrahydropyran
1a
has been previously synthesized through a cumbersome 9-step synthesis from tri-
O
-acetyl-D-glucal, which renders access to nemtabrutinib (
2
), a BTK inhibitor currently being evaluated for the treatment of various hematologic malignancies, inefficient and wasteful. Herein, we describe the development of a protecting group-free, 2-step synthesis of
1a
from Cyrene™, a biorenewable feedstock. The improved synthesis involves a biocatalytic transamination reaction of Cyrene™ to install the desired amine stereocenter in a single step with high diastereoselectivity. The enzymatic reaction is followed by a stereo-retentive reductive acetal opening reaction of the chiral cyrene amine intermediate
3a
to furnish
1a
. A mechanistic investigation of the acetal opening reaction is also described which uncovered reaction conditions for the sulfolane mediated
in situ
generation of diborane as the active reductant. The streamlined synthesis of
1a
from Cyrene™ reduced the step count from 9 to 2 synthetic steps which resulted in a >27% yield improvement and a significant reduction in the environmental impact of the synthesis.
The development of a protecting group-free, 2-step synthesis of 5-amino-2-hydroxymethyltetrahydropyran
1a
from biorenewable Cyrene™ is described which renders access to BTK-inhibitor nemtabrutinib (
2
) more efficient and sustainable. The chiral building block 5-amino-2-hydroxymethyltetrahydropyran 1a has been previously synthesized through a cumbersome 9-step synthesis from tri- O -acetyl-D-glucal, which renders access to nemtabrutinib (2), a BTK inhibitor currently being evaluated for the treatment of various hematologic malignancies, inefficient and wasteful. Herein, we describe the development of a protecting group-free, 2-step synthesis of 1a from Cyrene™, a biorenewable feedstock. The improved synthesis involves a biocatalytic transamination reaction of Cyrene™ to install the desired amine stereocenter in a single step with high diastereoselectivity. The enzymatic reaction is followed by a stereo-retentive reductive acetal opening reaction of the chiral cyrene amine intermediate 3a to furnish 1a. A mechanistic investigation of the acetal opening reaction is also described which uncovered reaction conditions for the sulfolane mediated in situ generation of diborane as the active reductant. The streamlined synthesis of 1a from Cyrene™ reduced the step count from 9 to 2 synthetic steps which resulted in a >27% yield improvement and a significant reduction in the environmental impact of the synthesis. The chiral building block 5-amino-2-hydroxymethyltetrahydropyran 1a has been previously synthesized through a cumbersome 9-step synthesis from tri-O-acetyl-D-glucal, which renders access to nemtabrutinib (2), a BTK inhibitor currently being evaluated for the treatment of various hematologic malignancies, inefficient and wasteful. Herein, we describe the development of a protecting group-free, 2-step synthesis of 1a from Cyrene™, a biorenewable feedstock. The improved synthesis involves a biocatalytic transamination reaction of Cyrene™ to install the desired amine stereocenter in a single step with high diastereoselectivity. The enzymatic reaction is followed by a stereo-retentive reductive acetal opening reaction of the chiral cyrene amine intermediate 3a to furnish 1a. A mechanistic investigation of the acetal opening reaction is also described which uncovered reaction conditions for the sulfolane mediated in situ generation of diborane as the active reductant. The streamlined synthesis of 1a from Cyrene™ reduced the step count from 9 to 2 synthetic steps which resulted in a >27% yield improvement and a significant reduction in the environmental impact of the synthesis. |
Author | Prier, Christopher K Chung, Cheol K Shang, Gao Newman, Justin A Rivera, Nelo R Zewge, Daniel Itoh, Tetsuji Reibarkh, Mikhail Kuhl, Nadine Thaisrivongs, David A Shevlin, Michael Larson, Reed T Wang, Zhixun Ji, Yining Desmond, Richard Turnbull, Ben W. H He, Cyndi Qixin Kuethe, Jeffrey T Guetschow, Erik |
AuthorAffiliation | Analytical Research and Development Process Research and Development Merck & Co Computational and Structural Chemistry Inc |
AuthorAffiliation_xml | – sequence: 0 name: Computational and Structural Chemistry – sequence: 0 name: Process Research and Development – sequence: 0 name: Merck & Co – sequence: 0 name: Inc – sequence: 0 name: Analytical Research and Development |
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CitedBy_id | crossref_primary_10_1021_acs_oprd_3c00018 crossref_primary_10_1016_j_jpba_2024_116002 crossref_primary_10_1021_acs_oprd_3c00510 crossref_primary_10_1021_acs_oprd_3c00218 crossref_primary_10_1021_acs_oprd_2c00391 crossref_primary_10_3390_chemistry5040154 crossref_primary_10_1021_jacsau_3c00103 crossref_primary_10_1002_cctc_202300560 crossref_primary_10_1021_acs_oprd_3c00395 crossref_primary_10_3390_molecules28041777 crossref_primary_10_1021_jacsau_2c00712 crossref_primary_10_1021_acscatal_3c04565 crossref_primary_10_1021_acscatal_3c00941 crossref_primary_10_1055_s_0042_1752683 crossref_primary_10_1021_acs_oprd_3c00374 |
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Notes | For ESI and crystallographic data in CIF or other electronic format see DOI https://doi.org/10.1039/d2gc04117k 2215968 Electronic supplementary information (ESI) available: For experimental procedures, compound characterization and crystallography data. CCDC 2215969 and |
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Snippet | The chiral building block 5-amino-2-hydroxymethyltetrahydropyran
1a
has been previously synthesized through a cumbersome 9-step synthesis from tri-
O... The chiral building block 5-amino-2-hydroxymethyltetrahydropyran 1a has been previously synthesized through a cumbersome 9-step synthesis from tri- O... The chiral building block 5-amino-2-hydroxymethyltetrahydropyran 1a has been previously synthesized through a cumbersome 9-step synthesis from... |
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SubjectTerms | Catalysis Diborane Environmental impact Green chemistry Malignancy Reducing agents Stereoselectivity Sulfolane |
Title | Utilizing biocatalysis and a sulfolane-mediated reductive acetal opening to access nemtabrutinib from cyrene |
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