Aluminium lithium hydride → HCID 71667999, compound

HRID 63326Notes

Reaction equation

HRID 63326 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([CH2:13][O:14][C:15]2[O:19][C:18]([CH:20]([OH:24])[CH2:21][C:22]#[N:23])=[CH:17][CH:16]=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:18]1[O:19][C:15]([O:14][CH2:13][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:16][CH:17]=1)[OH:24]

Participants

4

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21584172Ammonia methanol dichloromethaneHCID 86694622HCID 86694622, compound

Product 1

HCID 71667999HCID 71667999, compound

Procedure

LiAlH4 reduction of 3-(5-(cyclohexylmethoxy)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 24 as a light yellow oil which solidified upon standing. Yield (0.26 g, 46%); 1H NMR (400 MHz, CD3OD) δ 6.11 (d, J=3.4 Hz, 1H), 5.10 (d, J=3.4 Hz, 1H), 4.56 (t, J=6.8 Hz, 1H), 3.79 (d, J=6.3 Hz, 2H), 2.65-2.77 (m, 2H), 1.82-1.96 (m, 2H), 1.66-1.82 (m, 6H), 1.15-1.37 (m, 3H), 1.00-1.13 (m, 2H); ESI-MS m/z 254.2 [M+H]+.

Workup

  1. customgave
  2. customYield (0.26 g, 46%)

Sources & evidence

ORD record
ord-366b753289464298bbb750f128b0a971
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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