Potassium Carbonate → (S)-tert-Butyl 3-(2-hydroxyethyl)pyrrolidine-1-carboxylate

HRID 1761180Notes

Reaction equation

HRID 1761180 reaction equation
C([O:4][CH2:5][CH2:6][C@@H:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)(Cl)Cl>[OH:4][CH2:5][CH2:6][C@@H:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 697663351,1-Dimethylethyl (3S)-3-[2-(acetyloxy)ethyl]-1-pyrrolidinecarboxylate

Product 1

HCID 29942053(S)-tert-Butyl 3-(2-hydroxyethyl)pyrrolidine-1-carboxylateYield 101.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 34 mg of t-butyl(3S)-3-(2-acetyloxyethyl)pyrrolidine-1-carboxylate in 1 ml of methanol, 54 mg of potassium carbonate was added, and stirred for 2.5 hours at room temperature. The reaction liquid was diluted with chloroform, washed successively with water and saturated brine and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, 29 mg of the title compound was obtained.

Workup

  1. customThe reaction liquid
  2. washwashed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-bfa52baaa4cd43fcb64c8a566ae73f56
Source dataset
uspto-grants-2005_01
Patent number
US06846835B2

Reaction notes

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