Ethanol → HCID 44194660, compound

HRID 1192936Notes

Reaction equation

HRID 1192936 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2CC[C@:13]([CH2:22][C:23]([CH3:25])=[CH2:24])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][C:11]2=O)[CH3:9])=[CH:4][CH:3]=1.S([C:37]#[N:38])(C1C=CC(C)=CC=1)(=O)=O.C1([SiH3])C=CC=CC=1.[CH3:46][CH2:47][OH:48]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:11][CH2:12][C@:13]([CH2:22][C:23]([CH3:25])([CH3:24])[C:37]#[N:38])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:46][C:47]2=[O:48])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 12752PhenylsilaneHCID 87946p-Toluenesulphonyl cyanideHCID 67104684HCID 67104684, compound

Product 1

HCID 44194660HCID 44194660, compoundYield 50%

Procedure

A solution of (S)-1-((S)-1-(4-bromophenyl)ethyl)-4-(2-methylallyl)-4-phenylpiperidin-2-one (30 mg, 0.07 mmol), the cobalt(II) complex whose preparation is described below (0.46 mg, 0.0007 mmol), TsCN (19.8 mg, 0.11 mmol) and PhSiH3(8.4 mg, 0.08 mmol) in anhydrous EtOH (5 mL) was stirred at rt for 4 h. After the solvent was removed under reduced pressure, the residue was purified by preparative TLC to give 3-((S)-1-((S)-1-(4-bromophenyl)ethyl)-2-oxo-4-phenyl piperidin-4-yl)-2,2-di methylpropanenitrile (15 mg, 50%). LC-MS Method

Workup

  1. customAfter the solvent was removed under reduced pressure
  2. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-f97649b468734d7ca4ddcdfd63f68805
Source dataset
uspto-grants-2014_03
Patent number
US08680281B2

Reaction notes

Loading…