A Facile Method for the Preparation of MOM-Protected Carbamates

A novel method for the preparation of MOM-protected carbamates is described that avoids the use of MOM-Cl, a regulated carcinogen. The two-step, one-pot procedure generates a reactive N-chloromethyl carbamate that is quenched with methanol to afford MOM-protected carbamates. The process is tolerant...

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Bibliographic Details
Published inOrganic letters Vol. 11; no. 2; pp. 273 - 275
Main Authors Barnes, David M, Barkalow, Jufang, Plata, Daniel J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.01.2009
Amer Chemical Soc
Subjects
Carbamates - chemical synthesis
Carbamates - chemistry
Chemistry
Chemistry, Organic
Hydrogen-Ion Concentration
Methyl Chloride - chemistry
Methylation
Physical Sciences
Science & Technology
ENOLATE
CHIRALITY
ALKYLATION
AMINO-ACID DERIVATIVES
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Summary:A novel method for the preparation of MOM-protected carbamates is described that avoids the use of MOM-Cl, a regulated carcinogen. The two-step, one-pot procedure generates a reactive N-chloromethyl carbamate that is quenched with methanol to afford MOM-protected carbamates. The process is tolerant of a variety of functionalities, including Boc, sulfonamide, and acetamide protecting groups. Mild conditions for the removal of the MOM group are also described; selective deprotection of the MOM group in the presence of a Boc group has been demonstrated.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8022769