Scalable, efficient process for the synthesis of ( R)-3,5-bistrifluoromethylphenyl ethanol via catalytic asymmetric transfer hydrogenation and isolation as a DABCO inclusion complex
( R)-3,5-Bistrifluoromethylphenyl ethanol 2, a key building block in the synthesis of aprepitant, has been synthesized from ketone 5 via catalytic asymmetric transfer hydrogenation using a simplified catalyst generation procedure. The process uses (1 S,2 R)- cis-1-aminoindan-2-ol 10 and dichloro( p-...
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| Published in | Tetrahedron: asymmetry Vol. 14; no. 22; pp. 3581 - 3587 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
14.11.2003
Elsevier |
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| Abstract | (
R)-3,5-Bistrifluoromethylphenyl ethanol
2, a key building block in the synthesis of aprepitant, has been synthesized from ketone
5 via catalytic asymmetric transfer hydrogenation using a simplified catalyst generation procedure. The process uses (1
S,2
R)-
cis-1-aminoindan-2-ol
10 and dichloro(
p-cymene)Ru(II)dimer
9 as the chiral ligand and metal source for the reduction. While the reduction provides
2 in 90–92% ee, an isolation of
2 as a 2:1 inclusion complex with DABCO was developed to allow for the upgrade of the enantiomeric excess to >99%.
Graphic |
|---|---|
| AbstractList | (
R)-3,5-Bistrifluoromethylphenyl ethanol
2, a key building block in the synthesis of aprepitant, has been synthesized from ketone
5 via catalytic asymmetric transfer hydrogenation using a simplified catalyst generation procedure. The process uses (1
S,2
R)-
cis-1-aminoindan-2-ol
10 and dichloro(
p-cymene)Ru(II)dimer
9 as the chiral ligand and metal source for the reduction. While the reduction provides
2 in 90–92% ee, an isolation of
2 as a 2:1 inclusion complex with DABCO was developed to allow for the upgrade of the enantiomeric excess to >99%.
Graphic (R)-3,5-Bistrifluoromethylphenyl ethanol 2, a key building block in the synthesis of aprepitant, has been synthesized from ketone 5 via catalytic asymmetric transfer hydrogenation using a simplified catalyst generation procedure. The process uses (1S,2R)-cis-1-aminoindan-2-ol 10 and dichloro)-cymene)Ru(II)dimer 9 as the chiral ligand and metal source for the reduction. While the reduction provides 2 in 90-92% ee, an isolation of 2 as a 2:1 inclusion complex with DABCO was developed to allow for the upgrade of thee enantiomeric excess to >99%. (C) 2003 Elsevier Ltd. All rights reserved. |
| Author | Kubryk, Michele Mathre, David J. Devine, Paul N. Desmond, Richard Grabowski, Edward J.J. Varsolona, Richard Hansen, Karl B. Chilenski, Jennifer R. Heid, Richard |
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| Keywords | AROMATIC KETONES APREPITANT RECEPTOR ANTAGONIST |
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R)-3,5-Bistrifluoromethylphenyl ethanol
2, a key building block in the synthesis of aprepitant, has been synthesized from ketone
5 via catalytic asymmetric... (R)-3,5-Bistrifluoromethylphenyl ethanol 2, a key building block in the synthesis of aprepitant, has been synthesized from ketone 5 via catalytic asymmetric... |
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| SubjectTerms | Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Chemistry, Physical Physical Sciences Science & Technology |
| Title | Scalable, efficient process for the synthesis of ( R)-3,5-bistrifluoromethylphenyl ethanol via catalytic asymmetric transfer hydrogenation and isolation as a DABCO inclusion complex |
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