The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Feb. 21, 1995
Filed:
Jul. 08, 1993
Applicant:
Inventors:
Andrew S Thompson, Mountainside, NJ (US);
Edward J Grabowski, Westfield, NJ (US);
Assignee:
Merck & Co., Inc., Rahway, NJ (US);
Primary Examiner:
Assistant Examiner:
Int. Cl.
CPC ...
C07D / ; C07C / ;
U.S. Cl.
CPC ...
549492 ; 540557 ; 544336 ; 544242 ; 544256 ; 546329 ; 546176 ; 546139 ; 548561 ; 5483355 ; 5483097 ; 548254 ; 5483751 ; 548491 ; 548482 ; 548444 ; 548247 ; 548152 ; 548224 ; 548202 ; 548235 ; 549491 ; 549 74 ; 549467 ; 549 49 ; 549 23 ; 552 10 ;
Abstract
Described is a process for converting an alcohol to an azide with S.sub.N 2 inversion using a phosphoryl azide, e.g. diphenylphosphoryl azide (DPPA). Good yields of azide in high enantiomeric excess can be achieved specifically for benzylic alcohols and alpha-hydroxy alkyl esters. The process is carried at preferably room temperature in an inert dry aprotic solvent, e.g. toluene, and in the presence of a proton acceptor, e.g. 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to afford high yields of high enantiomeric purities.