Diethyl Ether → HCID 13911559, compound

HRID 653394Notes

Reaction equation

HRID 653394 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH2:13][CH:12]([C:14](OC)=[O:15])O[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O:21]CC)C>CO.O=[Pt]=O>[C:1]([O:5][C:6](=[O:18])[CH:7]([OH:21])[CH2:8][CH:9]1[CH2:13][CH2:12][C:14](=[O:15])[NH:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 13921017HCID 13921017, compound

Product 1

HCID 13911559HCID 13911559, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A suspension of 105 of 4,5-dihydro-5-methoxycarbonyl-3-isoxazolepropanoic acid t-butyl ester and 2.0 g of PtO2 /C in 1 L 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 titurated with anhydrous diethyl ether and filtered to yield 5-oxo-alpha-hydroxy-2-pyrrolidinepropanoic acid t-butyl ester as a white solid with mp 110°-112° C. NMR (CDCl3) and 6.38 (s, 1H), 4.13 (m, 1H), 3.87 (m, 1H), 3.27 (d, 1H), 2.47-1.60 (m, 6H), 7.53 (s, 9H). IR (KBr) 3460, 3245, 2978, 2938, 1723, 1686, 1426, 1392, 1372, 1318, 1277, 1256, 1209.

Workup

  1. customAfter H2 absorption
  2. filtrationthe solution is filtered
  3. customthe solvent removed under reduced pressure
  4. customto give an oil
  5. filtrationfiltered

Sources & evidence

ORD record
ord-9cae4944bda44dd0bff89dc840753ec1
Source dataset
uspto-grants-1987_06
Patent number
US04677098

Reaction notes

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