Water → HCID 22843275, compound

HRID 1029641Notes

Reaction equation

HRID 1029641 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14](OS(C)(=O)=O)[CH2:13][C@H:12]1[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:30]#[N:31].[Na+].O.C(OCC)(=O)C>CS(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([C:30]#[N:31])[CH2:13][C@H:12]1[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 15117255HCID 15117255, compound

Product 1

HCID 22843275HCID 22843275, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (2S,4R)-1-benzyloxycarbonyl-2-(tert-butyldimethylsilyloxy)methyl-4-methanesulfonyloxypyrrolidine (10.246 g) and sodium cyanide (3.6 g) in dimethyl sulfoxide (100 ml) was heated for three hours at 92° C. The reaction mixture was poured into a mixture of water (300 ml) and ethyl acetate (300 ml). The organic layer was separated, and the remaining aqueous layer was reextracted with ethyl acetate (200 ml). The organic layers were combined, 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 acetate (2:1, V/V) to give (2S,4S)-1-benzyloxycarbonyl-2-(tert-butyldimethylsilyloxy)methyl-4-cyanopyrrolidine (4.2 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 acetate (2:1, V/V)

Sources & evidence

ORD record
ord-eb50d98e2de7471a898a89512ededaa2
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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