Aluminium lithium hydride → HCID 86694663, compound

HRID 63349Notes

Reaction equation

HRID 63349 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C@@H:8]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:13]=1)[CH2:9][C:10]#[N:11].N.CO.C(Cl)Cl>>[NH2:11][CH2:10][CH2:9][C@H:8]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:13]=1)[OH:7]

Participants

4

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21584172Ammonia methanol dichloromethaneHCID 86694664HCID 86694664, compound

Product 1

HCID 86694663HCID 86694663, compound

Procedure

LiAlH4 reduction of (R)-3-hydroxy-3-(6-phenethoxypyridin-2-yl)propanenitrile following the method described in Example 1 gave after flash chromatography purification (20%-30% 7N NH3/MeOH—CH2Cl2 gradient) Example 41 as a colorless oil. Yield (0.13 g, 21%); 1H NMR (400 MHz, DMSO-d6) δ 7.62 (t, J=8.0 Hz, 1H), 7.28-7.16 (m, 5H), 7.02 (d, J=8.0 Hz, 1H), 6.60 (d, J=8.0 Hz, 1H), 4.70-4.68 (m, 1H), 4.78 (t, J=7.2 Hz, 2H), 3.05 (t, J=7.2 Hz, 2H), 2.78 (t, J=6.8 Hz, 2H), 2.04-1.82 (m, 2H); RP-HPLC tR=7.83 min; ESI-MS m/z 273.2 [M+H]+.

Workup

  1. customgave
  2. customYield (0.13 g, 21%)

Sources & evidence

ORD record
ord-d5254b98058748c48e513580d359b950
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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