2,2-Dipropyloxirane → 3-(Tert-butyldimethylsilyloxy)-3-(3-((1-hydroxycyclohexyl)methylamino)phenyl)propanenitrile
Reaction equation
[CH2:1]([C:4]1([CH2:7][CH2:8][CH3:9])[CH2:6][O:5]1)[CH2:2]C.[NH2:10][C:11]1[CH:12]=[C:13]([CH:17]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:18][C:19]#[N:20])[CH:14]=[CH:15][CH:16]=1>>[Si:22]([O:21][CH:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([NH:10][CH2:6][C:4]2([OH:5])[CH2:1][CH2:2][CH2:9][CH2:8][CH2:7]2)[CH:12]=1)[CH2:18][C:19]#[N:20])([C:25]([CH3:27])([CH3:28])[CH3:26])([CH3:24])[CH3:23]Participants
3
Procedure
Epoxide ring opening of 2,2-dipropyloxirane with 3-(3-aminophenyl)-3-(tert-butyldimethylsilyloxy)propanenitrile following the method used in Example 67 gave 3-(tert-butyldimethylsilyloxy)-3-(3-((1-hydroxycyclohexyl)methylamino)phenyl)propanenitrile as a colorless oil. Yield (1.5 g, 56%); 1H NMR (400 MHz, DMSO-d6) δ 7.01 (t, J=7.6 Hz, 1H), 6.63 (s, 1H), 6.57 (d, J=7.6 Hz, 1H), 6.52 (d, J=7.6 Hz, 1H), 5.22 (t, J=5.2 Hz, 1H), 4.91 (t, J=6.4 Hz, 1H), 4.21 (s, 1H), 2.84 (d, J=5.6 Hz, 2H), 2.78-2.75 (m, 2H), 1.77-1.39 (m, 10H), 0.87 (s, 9H), 0.05 (s, 3H), −0.05 (s, 3H).
Sources & evidence
- ORD record
- ord-530e3897cb99490b9df3b86f30f9fa56
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193669B2
Reaction notes
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