(S)-methyl 5-(4-(benzyloxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate → Methyl (5S)-5-{4-[(phenylmethyl)oxy]phenyl}-L-prolinate

HRID 2264796Notes

Reaction equation

HRID 2264796 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH2:16][CH2:17][C@@H:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.C(OCC)(=O)C.O=[Pt]=O>[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[NH:19][C@H:18]([C:20]([O:22][CH3:23])=[O:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 59164837(S)-methyl 5-(4-(benzyloxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

Product 1

HCID 59164828Methyl (5S)-5-{4-[(phenylmethyl)oxy]phenyl}-L-prolinate

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl (2S)-5-{4-[(phenylmethyl)oxy]phenyl}-3,4-dihydro-2H-pyrrole-2-carboxylate (D7, 13.7 g, 32.4 mmol) in MeOH (200 ml) was added PtO2 (240 mg) and the mixture was stirred under hydrogen atmosphere (2 atm) for 6 hours. Then the catalyst was filtered off and the solvent removed under reduced pressure to give a red oil which was dissolved in ethyl acetate and washed with NaHCO3 solution. The resulting crude material was purified by chromatography on silica gel eluting with cyclohexane/ethyl acetate (9:1 to 8:2) to afford the title compounds:

Workup

  1. filtrationThen the catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. customto give a red oil which
  4. washwashed with NaHCO3 solution
  5. customThe resulting crude material was purified by chromatography on silica gel eluting with cyclohexane/ethyl acetate (9:1 to 8:2)

Sources & evidence

ORD record
ord-e6483af8d666445c8c1c27ca4299fbd6
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

Loading…