Ammonia → HCID 18374571, compound

HRID 2300704Notes

Reaction equation

HRID 2300704 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[CH:10]([CH2:13][CH2:14][CH:15]([OH:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:9]2[C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1.N.[H][H].ClCCl.CO>C(O)C.[Ni]>[NH2:28][CH2:27][C:26]1[CH:29]=[CH:30][C:23]([CH:9]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:11](=[O:12])[CH:10]2[CH2:13][CH2:14][CH:15]([OH:22])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 18374574HCID 18374574, compoundHCID 21226129Dichloromethane methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 18374571HCID 18374571, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

930 mg of 4-[1-(4-fluorophenyl)-3-(3-hydroxy-3-phenylpropyl)-4-oxo-azetidin-2-yl]-benzonitrile, dissolved in 100 ml of ethanol, are admixed with 4 ml of conc. ammonia and hydrogenated for 20 hours over Raney Ni, at room temperature and a hydrogen pressure of 20 bar. The catalyst is filtered off and the filtrate is concentrated under reduced pressure, giving, after chromatography (SiO2, dichloromethane/methanol=0:1), the product of molecular weight 404.5 (C25H25FN2O2); MS (DCl+): 405 (M+H+), 387 (M+H+−H2O).

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customgiving

Sources & evidence

ORD record
ord-6c4a562aa938496791f6802e67b0dfed
Source dataset
uspto-grants-2002_12
Patent number
US06498156B2

Reaction notes

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