Water → Ethyl 1-benzyloxycarbonyl-4-hydroxy-3-methylpyrrolidine-3-carboxylate

HRID 446094Notes

Reaction equation

HRID 446094 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[C:13]([CH3:22])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+].O>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([OH:16])[C:13]([CH3:22])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 572801371-Benzyl 3-ethyl 3-methyl-4-oxopyrrolidine-1,3-dicarboxylate

Product 1

HCID 68861273Ethyl 1-benzyloxycarbonyl-4-hydroxy-3-methylpyrrolidine-3-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 1-benzyloxycarbonyl-3-methyl-4-oxopyrrolidine-3-carboxylate (1.0 g, 3.28 mmol) in methanol (20 mL), sodium borohydride (0.19 g, 4.92 mmol) was added at −20° C., and the mixture was stirred at the same temperature for 20 minutes. To the reaction mixture were added saturated aqueous solution of ammonium chloride (20 mL) and water (20 mL), and the mixture was extracted by ethyl acetate (20 mL×3). The extract was washed with saturated aqueous solution of sodium chloride (20 mL), and dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate, 3:1) to obtain 0.57 g (57%) of the title compound as a colorless oily product.

Workup

  1. extractionthe mixture was extracted by ethyl acetate (20 mL×3)
  2. washThe extract was washed with saturated aqueous solution of sodium chloride (20 mL)
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-bff08e57767d4a66af277ef2985cdb1e
Source dataset
uspto-grants-2013_07
Patent number
US08476429B2

Reaction notes

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