benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate → (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-4-ol

HRID 431757Notes

Reaction equation

HRID 431757 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][C@@H:21]([OH:23])[CH2:20][N:19]3C(OCC3C=CC=CC=3)=O)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][C@@H:21]([OH:23])[CH2:20][NH:19]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 86759290benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 11460944(2R, 4R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-4-olYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate (350 mg) in MeOH (15 mL) was added 10%Pd-C (wet) (50 mg), and the mixture was stirred under hydrogen atmosphere at room temperature for 1 hour. The catalyst was removed by filtration and the filtrate was evaporated to give (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-4-ol (236.8 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-0e86f3adec6f48368348bea596168505
Source dataset
uspto-grants-2003_12
Patent number
US06660759B1

Reaction notes

Loading…