Water → trans-Tert-butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate

HRID 1666673Notes

Reaction equation

HRID 1666673 reaction equation
C([O:4][C@H:5]1[C@H:9]([NH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:8][N:7]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH2:14]([O:13][C:11]([NH:10][C@H:9]1[C@H:5]([OH:4])[CH2:6][N:7]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:8]1)=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 57970174t-Butyl (3R,4R)-3-acetoxy-4-benzyloxycarbonylaminopyrrolidine-1-carboxylate

Product 1

HCID 57970124trans-Tert-butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxypyrrolidine-1-carboxylateYield 91.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

t-Butyl (3R,4R)-3-acetoxy-4-benzyloxycarbonylaminopyrrolidine-1-carboxylate (27 g) was dissolved in methanol (350 mL), followed by addition of potassium carbonate (16 g) with ice cooling, and the mixture was stirred overnight at room temperature. Water was added, and then the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1-2:1) to obtain t-butyl (3R,4R)-3-benzyloxycarbonylamino-4-hydroxypyrrolidine-1-carboxylate (22 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1-2:1)

Sources & evidence

ORD record
ord-5ece42eb747f405baec5313a3bff91f9
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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