(1R)-N-benzyloxycarbonyl-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butylamine → (1R)-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butylamine

HRID 1741367Notes

Reaction equation

HRID 1741367 reaction equation
C(OC([NH:11][C@@H:12]([C:17]1[O:18][C:19]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:21]=1)[CH2:13][CH2:14][CH2:15][OH:16])=O)C1C=CC=CC=1>CO.[Pd]>[OH:16][CH2:15][CH2:14][CH2:13][C@@H:12]([NH2:11])[C:17]1[O:18][C:19]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:21]=1

Participants

4

Reactant 1

HCID 53739918(1R)-N-benzyloxycarbonyl-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butylamine

Product 1

HCID 54014820(1R)-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butylamineYield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (1R)-N-benzyloxycarbonyl-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butylamine (12 g) and 10% Pd/C (2 g) in methanol (20 ml) was stirred under H2 for 5 hours. The catalyst was filtered off and filtrate was evaporated. The residue was recrystallized with ether to give (1R)-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butylamine (5.8 g). MS (m/z): 309 (M+ +1) NMR (CDCl3, δ): 1.7-2.0 (3H, m), 2.1-2.4 (1H, m), 2.6-2.8 (3H, m), 3.5-3.8 (2H, m), 4.0-4.2 (1H, m), 7.3-7.8 (10H, m)

Workup

  1. filtrationThe catalyst was filtered off
  2. customfiltrate was evaporated
  3. customThe residue was recrystallized with ether

Sources & evidence

ORD record
ord-e97f6f3abb644a7b8ec1d1341252d569
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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