Ethyl Acetate → HCID 18639167, compound

HRID 1650306Notes

Reaction equation

HRID 1650306 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[C:12](OC)=[O:13])=[O:6])[CH:2]=[CH2:3].[BH4-].[Na+].C(OCC)(=O)C>C(O)C.[Cl-].[Na+].O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:12][OH:13])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 15408611HCID 15408611, compound

Product 1

HCID 18639167HCID 18639167, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (2S)-1-allyloxycarbonyl-2 -methoxycarbonylpyrrolidine (2.0 g) in ethanol (30 ml) was added sodium borohydride (1.06 g) at 20° C. and the resulting mixture was allowed to stir for 18 hours at 20°-25° C. The reaction mixture was taken up into a mixture of brine (100 ml) and ethyl acetate (100 ml). The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (50 ml) eluting with a mixture of dichloromethane and acetone (20:1) to give (2S)-1-allyloxycarbonyl-2-hydroxymethylpyrrolidine (769.2 mg).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel (50 ml)
  5. washeluting with a mixture of dichloromethane and acetone (20:1)

Sources & evidence

ORD record
ord-a68f4154c3d048e58933a94618be4e0e
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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