Acetone → HCID 18642543, compound

HRID 703588Notes

Reaction equation

HRID 703588 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:26])[CH3:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CC(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:26])[CH3:25])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 18642545HCID 18642545, compound

Product 1

HCID 18642543HCID 18642543, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of {2S,4R)-1-benzyloxycarbonyl-2-(2-oxopropyl)oxymethyl-4-methanesulfonyloxypyrrolidine (12 g) in ethanol (120 ml) was added by portions sodium borohydride (2.4 g) at 0° C. After 7 hours, to the reaction mixture was added dropwise acetone (20 ml) carefully at 0° C. and the solvent was evaporated in vacuo. To the resultant residue were added ethyl acetate (200 ml) and water (100 ml), the organic layer was separated, washed with brine (100 ml) and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (500 ml) eluting with 5% methanol in dichloromethane (V/V) gave (2S,4R)-1-benzyloxycarbonyl-2-(2-hydroxypropyl)oxymethyl-4-methanesulfonyloxypyrrolidine (7.3 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionTo the resultant residue were added ethyl acetate (200 ml) and water (100 ml)
  3. customthe organic layer was separated
  4. washwashed with brine (100 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 5% methanol in dichloromethane (V/V)

Sources & evidence

ORD record
ord-06a50bae491045ae9cdf45110825319b
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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