Sodium Hydroxide → (2S,4S)-N-Allyloxycarbonyl-2-hydroxymethyl-4-mercaptopyrrolidine

HRID 2371821Notes

Reaction equation

HRID 2371821 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[C@H:7]([CH2:16][OH:17])[CH2:6]1)(=O)C.[OH-].[Na+]>CO>[CH2:13]([O:12][C:10]([N:8]1[CH2:9][C@@H:5]([SH:4])[CH2:6][C@H:7]1[CH2:16][OH:17])=[O:11])[CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 228426921-Pyrrolidinecarboxylic acid, 4-(acetylthio)-2-(hydroxymethyl)-, 2-propen-1-yl ester, (2S,4S)-

Product 1

HCID 22842694(2S,4S)-N-Allyloxycarbonyl-2-hydroxymethyl-4-mercaptopyrrolidineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2S,4S)-4-acetylthio-N-allyloxycarbonyl-2-hydroxymethylpyrrolidine (1.17 g, 4.5 mmol) in methanol (25 ml) was treated with 2N sodium hydroxide solution (4.95 ml) under ice-cooling, followed by stirring for 30 minutes, and partitioned between 6N hydrochloric acid (1.65 ml) and ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium chloride (30 ml×3), dried over anhydrous sodium sulfate, and evaporated to afford the title compound (875 mg, 90% yield) as an oil.

Workup

  1. temperaturecooling
  2. custompartitioned between 6N hydrochloric acid (1.65 ml) and ethyl acetate (100 ml)
  3. washThe organic layer was washed with saturated aqueous sodium chloride (30 ml×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-7c220df58539457387f91888d86abd37
Source dataset
uspto-grants-1992_03
Patent number
US05095013

Reaction notes

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