Acetone → (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-hydroxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

HRID 703581Notes

Reaction equation

HRID 703581 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][C:24](=[O:30])[CH2:25][C:26]([O:28][CH3:29])=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[CH3:33]C(C)=O>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][CH:24]([OH:30])[CH2:25][C:26]([O:28][CH2:29][CH3:33])=[O:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 57247318(2S,4R)-1-benzyloxycarbonyl-2-[{3-(methoxycarbonyl)-2-oxopropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

Product 1

HCID 57248032(2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-hydroxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-[{3-(methoxycarbonyl)-2-oxopropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (7 g) in ethanol (80 ml) was added by portions sodium borohydride (1.2 g) at 0° C. After 6 hours, to the reaction mixture was carefully added dropwise acetone (30 ml) at 0° C. and then the solvent was evaporated in vacuo. To the resultant residue were added ethyl acetate (100 ml) and water (50 ml). The organic layer was separated, washed with brine (50 ml) and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (500 ml) eluting with a mixture of dichloromethane and methanol (18:1 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-hydroxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (5.1 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionTo the resultant residue were added ethyl acetate (100 ml) and water (50 ml)
  3. customThe organic layer was separated
  4. washwashed with brine (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent
  7. customgave a residue, which
  8. customwas chromatographed on silica gel (500 ml)
  9. washeluting with a mixture of dichloromethane and methanol (18:1 V/V)

Sources & evidence

ORD record
ord-ad666784a6034ea898464939a7fe73bc
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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