Potassium Carbonate → (2S, 4S)-4-Hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1016072Notes

Reaction equation

HRID 1016072 reaction equation
C([O:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:12]([CH3:22])[CH2:11]1)(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[OH:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:12]([CH3:22])[CH2:11]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59556039HCID 59556039, compound

Product 1

HCID 56846373(2S, 4S)-4-Hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the ester of step B (1.0 g, 3.48 mmol) in MeOH (30 mL) was added K2CO3 (1.2 g, 8.7 mmol). After being stirred at room temperature for 4 hours, the solution was concentrated. The residue was taken up in ether. The resulting solution was washed with brine, dried over MgSO4 and concentrated. Flash chromatography eluting with a gradient of 0% to 20% to 40% EtOAc/hexanes provided 0.56 g of the title compound. MS calculated (M+H)+ 202. found 202.1.

Workup

  1. concentrationthe solution was concentrated
  2. washThe resulting solution was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. washFlash chromatography eluting with a gradient of 0% to 20% to 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-9bbc82eab11b4481bdc41d0453996864
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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