Ammonia → 4-(3-Aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one

HRID 2243605Notes

Reaction equation

HRID 2243605 reaction equation
[H][H].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:45])[CH2:11][CH2:12][CH:13]([C:31](N2C(C3C=CC=CC=3)COC2=O)=[O:32])[CH:14]([C:23]2[CH:30]=[CH:29][C:26](C#N)=[CH:25][CH:24]=2)[NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:6][CH:5]=1.[NH3:46].[CH2:47](O)C>[Ni]>[NH2:46][CH2:47][C:25]1[CH:24]=[C:23]([CH:14]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:31](=[O:32])[CH:13]2[CH2:12][CH2:11][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[OH:45])[CH:30]=[CH:29][CH:26]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 222520644-[5-(4-Fluorophenyl)-1-(4-fluorophenylamino)-5-hydroxy-2-(2-oxo-4-phenyloxazolidine-3-carbonyl)-pentyl]-benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 222520374-(3-Aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

In an autoclave, at a hydrogen pressure of 75 bar, 2.5 g of 3-{1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}benzonitrile 5 are reacted in 100 ml of ethanol and 15 ml of concentrated ammonia with 1.0 g of Raney-Nickel for 20 h. The reaction solution is filtered, concentrated and separated by silica gel chromatography (methylene chloride/methanol 10/1). This gives 15: C25H24F2N2O2 (422.48) MS (ESI) 405 (M+H—H2O)

Workup

  1. filtrationThe reaction solution is filtered
  2. concentrationconcentrated
  3. customseparated by silica gel chromatography (methylene chloride/methanol 10/1)

Sources & evidence

ORD record
ord-ef8f53f141794df699b7ac871bb3bc40
Source dataset
uspto-grants-2010_03
Patent number
US07674773B2

Reaction notes

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