Water → 1-Pyrrolidinecarboxylic acid, 4-cyano-2-(methoxymethyl)-, 1,1-dimethylethyl ester, (2S-cis)-

HRID 1029639Notes

Reaction equation

HRID 1029639 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10][C@H:9]1[CH2:18][O:19][CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:21]#[N:22].[Na+].O.C(OCC)(=O)C>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:21]#[N:22])[CH2:10][C@H:9]1[CH2:18][O:19][CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 15117248HCID 15117248, compound

Product 1

HCID 151172491-Pyrrolidinecarboxylic acid, 4-cyano-2-(methoxymethyl)-, 1,1-dimethylethyl ester, (2S-cis)-Yield 97.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-methanesulfonyloxy-2-methoxymethylpyrrolidine (3.3 g) and sodium cyanide (1.75 g) in dimethyl sulfoxide (35 ml) was heated for three hours and forty minutes at 92° C. The reaction mixture was poured into a mixture of water (100 ml) and ethyl acetate (100 ml). The organic layer was separated, washed with brine, and dried over magnesium sulfate. Evaporation of the solvent gave an oil, which was chromatographed on silica gel (200 ml) eluting with a mixture of hexane and ethyl (1:1, V/V) to give (2S,4S)-1-(tert-butoxycarbonyl)-4-cyano-2-methoxymethylpyrrolidine (2.5 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave an oil, which
  6. customwas chromatographed on silica gel (200 ml)
  7. washeluting with a mixture of hexane and ethyl (1:1, V/V)

Sources & evidence

ORD record
ord-232651157a4c40dba39016715c8ea519
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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