Water → HCID 15227833, compound

HRID 1733931Notes

Reaction equation

HRID 1733931 reaction equation
C(OC([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:23][CH:22]([CH2:24][N:25]3[CH2:30][CH2:29][CH:28]([O:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:27][CH2:26]3)[O:21][C:20]2=[O:40])=[CH:15][CH:14]=1)=O)C1C=CC=CC=1.C(OC(NCC1C=CC(N2CC(CCl)OC2=O)=CC=1)=O)C1C=CC=CC=1.N1CCC(OCC(OC(C)(C)C)=O)CC1.O>CO.[Pd].[C].C(O)(=O)C>[NH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:23][CH:22]([CH2:24][N:25]3[CH2:26][CH2:27][CH:28]([O:31][CH2:32][C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[CH2:29][CH2:30]3)[O:21][C:20]2=[O:40])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10036224Tert-butyl (piperidin-4-yloxy)-acetateHCID 15227832HCID 15227832, compoundHCID 19439025HCID 19439025, compound

Product 1

HCID 15227833HCID 15227833, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 1 g of tert-butyl 1-(3-(4-benzyloxycarbonylaminomethylphenyl)-2-oxo-5-oxazolidinylmethyl)piperidine-4-oxyacetate (obtainable from 3-(4-benzyloxycarbonylaminomethylphenyl)-5-chloromethyl-2-oxazolidinone and tert-butyl piperidine-4-oxyacetate in accordance with the method described in Example 3) in a mixture of 38 ml of methanol, 6 ml of water and 6 ml of acetic acid is hydrogenated on 0.6 g of 5% Pd-carbon at 20° and 1 bar until H2 uptake has ceased. The mixture is filtered and the filtrate is concentrated by evaporation, and tert-butyl 1-(3-(4-aminomethylphenyl)-2-oxo-5-oxazolidinylmethyl)piperidine-4-oxyacetate is obtained, m.p. 95°-96°, FAB 420.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-8e1628186fad40f49a7838e9efeb025e
Source dataset
uspto-grants-1996_07
Patent number
US05532255

Reaction notes

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