Aluminium lithium hydride → (E)-3-amino-1-(5-(2-cyclohexylvinyl)pyridin-3-yl)propan-1-ol

반응식

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1(/[CH:13]=[CH:14]/[C:15]2[CH:16]=[C:17]([CH:21]([OH:25])[CH2:22][C:23]#[N:24])[CH:18]=[N:19][CH:20]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.N.CO.C(Cl)Cl>>[NH2:24][CH2:23][CH2:22][CH:21]([C:17]1[CH:18]=[N:19][CH:20]=[C:15](/[CH:14]=[CH:13]/[CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:16]=1)[OH:25]

참가 물질

반응물 3

HCID 21226445Aluminium lithium hydride

HCID 21584172Ammonia methanol dichloromethane

HCID 86694594(E)-3-(5-(2-cyclohexylvinyl)pyridin-3-yl)-3-hydroxypropanenitrile

생성물 1

HCID 86694595(E)-3-amino-1-(5-(2-cyclohexylvinyl)pyridin-3-yl)propan-1-ol

실험 절차

LiAlH4 reduction of (E)-3-(5-(2-cyclohexylvinyl)pyridin-3-yl)-3-hydroxypropanenitrile following the method used in Example 3 gave after flash chromatography purification (10%-30% 7N NH3/MeOH—CH2Cl2 gradient) Example 10 as a light yellow oil. Yield (0.5 g, 59%); 1H NMR (400 MHz, CD3OD) δ 8.37 (d, J=2.0 Hz, 1H), 8.33 (d, J=1.5 Hz, 1H), 7.85 (t, J=2.0 Hz, 1H), 6.40-6.38 (m, 2H), 4.84-4.76 (m, 1H), 2.86-2.78 (m, 2H), 2.24-2.08 (m, 1H), 1.98-1.66 (m, 7H), 1.44-1.28 (m, 5H); RP-HPLC tR=6.23 min; ESI-MS m/z 261.2 [M+H]+.