p-Cyanobenzal-p-anisidine → 1-(4-Aminomethylphenyl)-3-[3-hydroxy-3-phenylpropyl]-4-phenylazetidin-2-one

HRID 2241879Notes

Reaction equation

HRID 2241879 reaction equation
COC1C=CC(N=CC2C=CC(C#N)=CC=2)=CC=1.[CH:19](=[N:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.F[C:36]1[CH:41]=[CH:40][C:39]([CH:42]([OH:60])[CH2:43][CH2:44][CH2:45][C:46](N2C(C3C=CC=CC=3)COC2=O)=[O:47])=[CH:38][CH:37]=1.C1(C(O)CCCC(N2C(C3C=CC=CC=3)COC2=O)=O)C=CC=CC=1>[Ni]>[NH2:32][CH2:31][C:30]1[CH:29]=[CH:28][C:27]([N:26]2[CH:19]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:45]([CH2:44][CH2:43][CH:42]([OH:60])[C:39]3[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=3)[C:46]2=[O:47])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 259759p-Cyanobenzal-p-anisidineHCID 2621774-(Benzylideneamino)benzonitrileHCID 121116173-[5-(4-Fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-2-oxazolidinoneHCID 183745813-(5-Hydroxy-5-phenylpentanoyl)-4-phenyl-1,3-oxazolidin-2-one

Product 1

HCID 210831701-(4-Aminomethylphenyl)-3-[3-hydroxy-3-phenylpropyl]-4-phenylazetidin-2-one

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Compound (16) was prepared as described in example IIIa-d, the differences being that: a) instead of 4-[(4-methoxyphenylimino)methyl]benzonitrile, 4-(benzylideneamino)benzonitrile was used, b) instead of 3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl-4-phenyloxazolidin-2-one, 3-[5-(phenyl)-5-hydroxypentanoyl]-4-phenyl-oxazolidin-2-one was used, and c) the product IIId was subjected to reduction with Raney nickel.

Sources & evidence

ORD record
ord-1fdd54ef934448c9b37143de1d16facc
Source dataset
uspto-grants-2010_03
Patent number
US07671047B2

Reaction notes

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