Aluminium lithium hydride → HCID 86694595, compound

HRID 63308Notes

Reaction equation

HRID 63308 reaction equation
[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]

Participants

4

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21584172Ammonia methanol dichloromethaneHCID 86694594(E)-3-(5-(2-cyclohexylvinyl)pyridin-3-yl)-3-hydroxypropanenitrile

Product 1

HCID 86694595HCID 86694595, compound

Procedure

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]+.

Workup

  1. customgave
  2. customYield (0.5 g, 59%)

Sources & evidence

ORD record
ord-1e36a3753ced45a9a4f0165af6868e34
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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