HCID 70102315, compound → HCID 22087109, compound

HRID 2227434Notes

Reaction equation

HRID 2227434 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C@@H:14]3[O:18][C:17](=[O:19])[N:16]([C:20]4[CH:25]=[CH:24][C:23]([O:26]CC5C=CC=CC=5)=[CH:22][CH:21]=4)[CH2:15]3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1>CO.[Ni]>[F:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C@@H:14]3[O:18][C:17](=[O:19])[N:16]([C:20]4[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=4)[CH2:15]3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 70102315HCID 70102315, compound

Product 1

HCID 22087109HCID 22087109, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

At atmospheric pressure and 20° C., a solution of 1 g of (5S)-(−)-5-[4-(4-fluorobenzyl)-1-piperidinyl-methyl]-3-(4-benzyloxyphenyl)oxazolidin-2-one [obtainable by reaction of (5R)-(−)-5-(methanesulfonyloxy-methyl) -3-p-benzyloxyphenyloxazolidin-2-one with 4- (4-fluorobenzyl)piperidine hydrochloride] in 25 ml of methanol is hydrogenated over 1 g of Raney nickel. The mixture is filtered and the solvent is removed, giving (5S)-(−)-5-[4-(4-fluorobenzyl)-1-piperidinylmethyl]-3-(4-hydroxyphenyl) oxazolidin-2-one,

Workup

  1. customAt atmospheric pressure and 20° C.
  2. filtrationThe mixture is filtered
  3. customthe solvent is removed

Sources & evidence

ORD record
ord-026f236fb93c4ec7a43c44aaca2faa60
Source dataset
uspto-grants-2002_07
Patent number
US06413989B1

Reaction notes

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