Water → (2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-(2-azidoethyl) pyrrolidine

HRID 975698Notes

Reaction equation

CC(C)([O-])C.[K+].[C:7]([OH:10])(=[S:9])[CH3:8].[CH2:11]([O:14][C:15]([N:17]1[CH2:21][C@H:20](OS(C)(=O)=O)[CH2:19][C@H:18]1[CH2:27][CH2:28][N:29]=[N+:30]=[N-:31])=[O:16])[CH:12]=[CH2:13].O>CN(C)C=O.C(OCC)(=O)C>[C:7]([S:9][C@@H:20]1[CH2:21][N:17]([C:15]([O:14][CH2:11][CH:12]=[CH2:13])=[O:16])[C@H:18]([CH2:27][CH2:28][N:29]=[N+:30]=[N-:31])[CH2:19]1)(=[O:10])[CH3:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of potassium t-butoxide (6.99 g) in dimethylformamide (150 ml) was added thioacetic acid (4.45 ml) under ice-cooling. After stirring for 15 minutes, a solution of (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-methanesulfonyloxypyrrolidine (15.3 g) in dimethylformamide (20 ml) was added to the mixture under ice-cooling. The mixture was warmed to 80° C. and stirred for 4 hours, then cooled to ambient temperature and poured into water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with sat. sodium bicarbonate, water (twice) and brine, dried over magnesium sulfate, and evaporated under reduced pressure to give (2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-(2-azidoethyl) pyrrolidine (14.7 g).

Workup

temperaturecooling
temperaturecooling
stirringstirred for 4 hours
temperaturecooled to ambient temperature
customThe organic layer was separated
extractionthe aqueous layer was extracted twice with ethyl acetate
washThe combined organic layer was washed with sat. sodium bicarbonate, water (twice) and brine
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-26b19d95bd91486c91895e71949fb07a
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608056

Reaction notes

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