Phenylsilane → 6-(2-Hydroxy-2-methylpropyl)-3-(1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)cyclopropyl)-6-phenyl-1,3-oxazinan-2-one

HRID 1422657Notes

Reaction equation

HRID 1422657 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([N:17]4[CH2:22][CH2:21][C:20]([CH2:29][C:30]([CH3:32])=[CH2:31])([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[O:19][C:18]4=[O:33])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][C:3]1=[O:34].C1([SiH3])C=CC=CC=1.CC([OH:45])C.C(Cl)Cl>[Co]>[OH:45][C:30]([CH3:32])([CH3:31])[CH2:29][C:20]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:19][C:18](=[O:33])[N:17]([C:14]2([C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:6]=[CH:7][N:2]([CH3:1])[C:3](=[O:34])[CH:4]=4)=[CH:13][CH:12]=3)[CH2:16][CH2:15]2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 12752PhenylsilaneHCID 21966342Isopropanol methylene chlorideHCID 509059523-(1-(4-(1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 509059536-(2-Hydroxy-2-methylpropyl)-3-(1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)cyclopropyl)-6-phenyl-1,3-oxazinan-2-oneYield 30%

Reagents, catalysts & solvents 1

HCID 104730CobaltCatalyst

Procedure

To a solution of 3-(1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (22 mg, 0.048 mmol) in 2:1 2-Propanol/CH2Cl2 (1.5 mL) was added cobalt catalyst A (catalytic amount, c.a. 1 mg), followed by addition of phenylsilane (100 μL, excess). The mixture was stirred vigorously in open air for 1 h. LC-MS found the reaction was complete. The mixture was quenched with 3% aq HCl, filtered, and purified by prep HPLC to afford the title compound (6.8 mg, 30%). LC-MS Method 1 tR=1.37 min., m/z 473 (M+1); 1H NMR (CD3OD) δ 7.69(d, 1H), 7.54(d, 2H), 7.42-7.39(m, 5H), 7.13(d, 2H), 6.74(s, 1H), 6.69(d, 1H), 3.59(s, 3H), 3.25(m, 1H), 2.89(m, 1H), 2.67-2.50(m, 2H), 2.19(s, 2H), 1.36-1.20(m, 3H), 1.25(s, 3H), 1.09(m, 1H), 0.95(s, 3H).

Workup

  1. customThe mixture was quenched with 3% aq HCl
  2. filtrationfiltered
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-094f05c21aee40d6b94b3bfda01a0249
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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