Aluminium lithium hydride → (E)-3-amino-1-(4-(2-cyclohexylvinyl)thiophen-2-yl)propan-1-ol

HRID 63310Notes

Reaction equation

HRID 63310 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:23])[C:21]#N)[S:18][CH:19]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.N.CO.C(Cl)Cl.C1(COC2[N:43]=[C:42](C(OC)=O)C=CC=2)CCCCC1>>[NH2:43][CH2:42][CH2:21][CH:20]([C:17]1[S: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:23]

Participants

5

Reactant 4

HCID 21226445Aluminium lithium hydrideHCID 21584172Ammonia methanol dichloromethaneHCID 86694599HCID 86694599, compoundHCID 86694600HCID 86694600, compound

Product 1

HCID 86694598(E)-3-amino-1-(4-(2-cyclohexylvinyl)thiophen-2-yl)propan-1-ol

Procedure

LiAlH4 reduction of (E)-2-(4-(2-cyclohexylvinyl)thiophen-2-yl)-2-hydroxyacetonitrile following the method used in Example 3 gave after flash chromatography purification (20%-30% 7N NH3/MeOH—CH2Cl2 gradient) Example 13 as a light yellow oil. Yield (0.44 g, 36%); 1H NMR (400 MHz, DMSO-d6) δ 7.19 (s, 1H), 7.13 (s, 1H), 6.25 (d, J=16.8 Hz, 1H), 5.98 (dd, J=16.0, 6.4 Hz, 1H), 4.84 (t, J=6.0 Hz, 1H), 2.72-2.58 (m, 2H), 2.24-2.08 (m, 1H), 1.78-1.58 (m, 7H), 1.38-1.02 (m, 5H); RP-HPLC tR=10.49 min; ESI-MS m/z 219.1.2 [M+H]+.

Workup

  1. customgave
  2. customYield (0.44 g, 36%)

Sources & evidence

ORD record
ord-3135007f37884b0ca7337b4bca70dddd
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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