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1. (WO1995001970) ALCOHOL TO AZIDE SN¿2? CONVERSION
Latest bibliographic data on file with the International Bureau   

Pub. No.: WO/1995/001970 International Application No.: PCT/US1994/007524
Publication Date: 19.01.1995 International Filing Date: 05.07.1994
Chapter 2 Demand Filed: 06.02.1995
IPC:
C07C 247/06 (2006.01) ,C07D 213/42 (2006.01) ,C07D 215/12 (2006.01) ,C07D 307/52 (2006.01) ,C07D 307/78 (2006.01) ,C07D 333/20 (2006.01) ,C07D 333/54 (2006.01) ,C07D 333/58 (2006.01) ,C07D 495/04 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
247
Compounds containing azido groups
02
with azido groups bound to acyclic carbon atoms of a carbon skeleton
04
being saturated
06
and containing rings
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
213
Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
02
having three double bonds between ring members or between ring members and non-ring members
04
having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
24
with substituted hydrocarbon radicals attached to ring carbon atoms
36
Radicals substituted by singly-bound nitrogen atoms
42
having hetero atoms attached to the substituent nitrogen atom
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
215
Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
02
having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
12
with substituted hydrocarbon radicals attached to ring carbon atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
307
Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
02
not condensed with other rings
34
having two or three double bonds between ring members or between ring members and non-ring members
38
with substituted hydrocarbon radicals attached to ring carbon atoms
52
Radicals substituted by nitrogen atoms not forming part of a nitro radical
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
307
Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
77
ortho- or peri-condensed with carbocyclic rings or ring systems
78
Benzo [b] furans; Hydrogenated benzo [b] furans
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
333
Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
02
not condensed with other rings
04
not substituted on the ring sulfur atom
06
with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
14
Radicals substituted by singly bound hetero atoms other than halogen
20
by nitrogen atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
333
Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
50
condensed with carbocyclic rings or ring systems
52
Benzo [b] thiophenes; Hydrogenated benzo [b] thiophenes
54
with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
333
Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
50
condensed with carbocyclic rings or ring systems
52
Benzo [b] thiophenes; Hydrogenated benzo [b] thiophenes
54
with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
58
Radicals substituted by nitrogen atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
495
Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
02
in which the condensed system contains two hetero rings
04
Ortho-condensed systems
Applicants:
MERCK & CO., INC. [US/US]; 126 East Lincoln Avenue Rahway, NJ 07065, US
Inventors:
THOMPSON, Andrew, S.; US
GRABOWSKI, Edward, J., J.; US
Agent:
NORTH, Robert, J.; Merck & Co., Inc. Patent Department 126 East Lincoln Avenue Rahway, NJ 07065-0907, US
Common
Representative:
MERCK & CO., INC.; Patent Dept. 126 East Lincoln Avenue Rahway, NJ 07065, US
Priority Data:
089,31508.07.1993US
Title (EN) ALCOHOL TO AZIDE SN2 CONVERSION
(FR) CONVERSION D'ALCOOL EN AZIDE PAR SN2
Abstract:
(EN) Described is a process for converting an alcohol to an azide with SN2 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.
(FR) Ce procédé qui permet la conversion d'alcool en azide par inversion SN2 en utilisant un azide alcoylique tel que le diphényl du phosphore (DPPA), donne de bonnes proportions d'azide en fort excédent énantiomorphe, notamment dans le cas des alcools benzoïques et des esters alcoyliques alpha-hydroxyliques. Le procédé se réalise de préférence à température ambiante en solution aprotique sèche inerte telle que la solution de toluène, en présence d'un accepteur de protons tel que le 1,8-diazabicyclo[5.4.0]undéc-7-ène (DBU) afin d'obtenir un taux élevé de pureté énantiomorphe.
Designated States: AU, BB, BG, BR, BY, CA, CN, CZ, FI, GE, HU, JP, KE, KG, KR, KZ, LK, LT, LV, MD, MG, MN, MW, NO, NZ, PL, RO, RU, SD, SI, SK, TJ, TT, UA, UZ
European Patent Office (EPO) (AT, BE, CH, DE, DK, ES, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)