Methanol → HCID 13911556, compound

HRID 653393Notes

Reaction equation

HRID 653393 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[CH2:10][CH:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])O[N:7]=1.C[OH:20]>O=[Pt]=O>[C:14]([O:13][C:11](=[O:12])[CH2:9][CH2:10][CH:6]1[CH2:5][CH:4]([OH:20])[C:3](=[O:2])[NH:7]1)([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 887MethanolHCID 13911555HCID 13911555, compound

Product 1

HCID 13911556HCID 13911556, compound

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

A suspension of 40 g of 4,5-dihydro-5-t-butoxycarbonyl-3-isoxazole-propanoic acid methyl ester and 2.0 g of PtO2 /C in 400 ml of methanol is placed under a hydrogen atmosphere with agitation. After H2 absorption is complete, the solution is filtered and the solvent removed under reduced pressure to give an oil. The oil is triturated with anhydrous diethyl ether to yield 4-hydroxy-5-oxo-2-pyrrolidinepropanoic acid t-butyl ester as a white solid with mp 94°-95° C. NMR (CDCl3) and 6.83 (s, 1H), 4.42 (m, 1H), 3.93 (s, 1H), 3.70 (m, 1H), 2.78-1.66 (m, 6H), 1.47 (s, 9H). IR (KBr) 3320, 2980, 1732, 1705, 1456, 1417, 1353, 1368, 1295, 1260, 1214.

Workup

  1. customAfter H2 absorption
  2. filtrationthe solution is filtered
  3. customthe solvent removed under reduced pressure
  4. customto give an oil
  5. customThe oil is triturated with anhydrous diethyl ether

Sources & evidence

ORD record
ord-6272776448d14f11baf649a70fb8e62d
Source dataset
uspto-grants-1987_06
Patent number
US04677098

Reaction notes

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