(2R)-1-benzyloxycarbonyl-2-(4,5-diphenyloxazol-2-yl)pyrrolidine → (2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidine

HRID 1741378Notes

Reaction equation

HRID 1741378 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16]1[O:17][C:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:20]=1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[C:21]1([C:19]2[N:20]=[C:16]([C@H:12]3[CH2:13][CH2:14][CH2:15][NH:11]3)[O:17][C:18]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 54511676(2R)-1-benzyloxycarbonyl-2-(4,5-diphenyloxazol-2-yl)pyrrolidine

Product 1

HCID 15505347(2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (2R)-1-benzyloxycarbonyl-2-(4,5-diphenyloxazol-2-yl)pyrrolidine (4 g) and 10% Pd/C (0.5 g) in ethanol (120 ml) was stirred under H2 for 10 hours. The catalyst was filtered off and filtrate was evaporated in vacuo to give (2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidine. NMR (CDCl3, δ): 1.7-2.3 (4H, m), 2.9-3.2 (2H, m), 3.6-3.8 (1H, m), 4.44 (1H, t, J=6.0 Hz), 7.2-7.7 (10H, m)

Workup

  1. filtrationThe catalyst was filtered off
  2. customfiltrate was evaporated in vacuo

Sources & evidence

ORD record
ord-f1bed89a7a704224a25c409958d40417
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

Loading…