Sodium Benzoate → (2S,4S)-1-tert-Butyl 2-methyl 4-(benzoyloxy)pyrrolidine-1,2-dicarboxylate

HRID 2073248Notes

Reaction equation

HRID 2073248 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13]S(C)(=O)=O)[CH2:10][C@H:9]1[C:18]([O:20][CH3:21])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]([O-])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Na+]>CS(C)=O.C(OCC)(=O)C>[C:22]([O:13][C@@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:18]([O:20][CH3:21])=[O:19])[CH2:10]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 517055Sodium BenzoateHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 10760219(2S,4S)-1-tert-Butyl 2-methyl 4-(benzoyloxy)pyrrolidine-1,2-dicarboxylateYield 88.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (2S,4R)-1-t-butoxycarbonyl-4-methylsulfonyloxy-2-methoxycarbonylpyrrolidine (32.3 g) and sodium benzoate (28.8 g) in dimethyl sulfoxide (320 ml) was stirred at 90° C. overnight and cooled to room temperature. The mixture was diluted with ethyl acetate (600 ml) and washed successively with water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give an oil. The oil was crystallized from n-hexane to give (2S,4S)-4-benzoyloxy-1-t-butoxycarbonyl-2-methoxycarbonylpyrrolidine (31.0 g) as a colorless crystal.

Workup

  1. temperaturecooled to room temperature
  2. washwashed successively with water and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customto give an oil
  6. customThe oil was crystallized from n-hexane

Sources & evidence

ORD record
ord-a28dfee4e1f7409eaeb4e6ae414c41ae
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

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