Sodium Hydroxide → (2R,3R)-1-(tert-Butoxycarbonyl)-2-phenylpyrrolidine-3-carboxylic acid

HRID 130621Notes

Reaction equation

HRID 130621 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:7]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:5])C.[OH-].[Na+]>CO>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C@@H:6]([C:4]([OH:5])=[O:3])[C@@H:7]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131726910HCID 131726910, compound

Product 1

HCID 57354967(2R,3R)-1-(tert-Butoxycarbonyl)-2-phenylpyrrolidine-3-carboxylic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

trans-2-Phenyl-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (obtained from preparatory example 3) (0.68 g, 2.13 mmol) was stirred in a solution of 10.5 mL of 1M NaOH and 10.5 mL of methanol at rt for 2 days. The mixture was concentrated, acidified with 6 M HCl (aq) to pH ˜2, and extracted 3× with CH2Cl2. The combined extracts were dried through cotton, and concentrated. Silica gel chromatography eluting with hexanes/ethyl acetate (1:1) gave 0.58 g of a colorless oil. Crystallization from pet. ether/ether (ca. 10:1; 25 mL) gave 0.427 g (69%) of the title compound. MS APCI: [M+H]+=292.1

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted 3× with CH2Cl2
  3. customThe combined extracts were dried through cotton
  4. concentrationconcentrated
  5. washSilica gel chromatography eluting with hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-0a87de974337438d98142cca5a5cdfcc
Source dataset
uspto-grants-2008_06
Patent number
US07381741B2

Reaction notes

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