Ethanol → HCID 59627247, compound

HRID 1523264Notes

Reaction equation

HRID 1523264 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][C:23]([CH3:25])=[CH2:24])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:12]C2=O)[CH3:9])=[CH:4][CH:3]=1.S([C:37]#[N:38])(C1C=CC(C)=CC=1)(=O)=O.C(OO)(C)(C)C.C1([SiH3])C=CC=CC=1.C[CH2:53][OH:54]>[Co]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][C:23]([CH3:24])([CH3:25])[C:37]#[N:38])([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:12][C:53]2=[O:54])[CH3:9])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 6410tert-Butyl hydroperoxideHCID 12752PhenylsilaneHCID 87946p-Toluenesulphonyl cyanideHCID 59627202HCID 59627202, compound

Product 1

HCID 59627247HCID 59627247, compoundYield 4.5%

Reagents, catalysts & solvents 1

HCID 104730CobaltCatalyst

Procedure

Cobalt catalyst 1 (1.32 mg, 0.002 mmol, 1 mol %) was dissolved in EtOH (8 mL; absolute) at rt under argon, (R)-1-((S)-1-(4-bromophenyl)ethyl)-4-(2-methylallyl)-4-phenyltetrahydropyrimidin-2(1H)-one (82.6 mg, 0.2 mmol), TsCN (54 mg, 0.3 mmol), tBuOOH (6 mg, 0.06 mmol), and PhSiH3 (21.6 mg, 0.2 mmol) were added. The resulting solution was stirred at rt for 3 h. The solvent was removed by evaporation, and the residue was purified by prep HPLC to afford 3-((R)-1-((S)-1-(4-bromophenyl)ethyl)-2-oxo-4-phenylhexahydropyrimidin-4-yl)-2,2-dimethylpropanenitrile (4 mg, 4.5%) as a white solid. 1H NMR (CD3OD): δ 1.24 (s, 3H), 1.36 (s, 3H), 1.47-1.48 (m, 3H), 2.04-2.07 (m, 2H), 2.07 (m, 1H), 2.22-2.26 (m, 2H), 2.98-3.02 (m, 1H), 5.65-5.67 (m, 1H), 6.95-6.97 (m, 1H), 7.25-7.30 (m, 3H), 7.33-7.37 (m, 4H).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-b28e4256e2644f609f32cb5a12358d19
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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