Aluminium lithium hydride → HCID 86694613, compound

HRID 63320Notes

Reaction equation

HRID 63320 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1(/[CH:13]=[CH:14]/[C:15]2[CH:16]=[C:17]([CH:20]([OH:24])[CH2:21][C:22]#[N:23])[O:18][CH:19]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.N.CO.C(Cl)Cl>>[NH2:23][CH2:22][CH2:21][CH:20]([C:17]1[O:18][CH:19]=[C:15](/[CH:14]=[CH:13]/[CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:16]=1)[OH:24]

Participants

4

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21584172Ammonia methanol dichloromethaneHCID 86694614HCID 86694614, compound

Product 1

HCID 86694613HCID 86694613, compound

Procedure

LiAlH4 reduction of (E)-3-(4-(2-cyclohexylvinyl)furan-2-yl)-3-hydroxypropanenitrile following the method used in Example 1 gave after flash chromatography purification (2%-20% 7N NH3/MeOH—CH2Cl2 gradient) Example 22 as a colorless oil. Yield (0.07 g, 53%); 1H NMR (400 MHz, CD3OD) δ 7.34 (s, 1H), 6.41 (s, 1H), 6.17 (d, J=17.2 Hz, 1H), 5.88 (dd, J=7.3, 16.1 Hz, 1H), 4.67 (t, J=6.9 Hz, 1H), 2.67-2.80 (m, 2H), 2.00-2.10 9m, 1H), 1.90-2.00 (m, 2H), 1.63-1.81 (m, 5H), 1.10-1.40 (m, 5H); RP-HPLC tR=10.42 min; ESI-MS m/z 232.2 [M−H2O+H]+.

Workup

  1. customgave
  2. customYield (0.07 g, 53%)

Sources & evidence

ORD record
ord-78c009b587ad43e8a4647b1d15497cf7
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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