Aluminium lithium hydride → (R)-3-amino-1-(6-(cyclopentylmethoxy)pyridin-2-yl)propan-1-ol

HRID 63339Notes

Reaction equation

HRID 63339 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([CH2:12][O:13][C:14]2[N:19]=[C:18]([C@H:20]([OH:24])[CH2:21][C:22]#[N:23])[CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1.N.CO.C(Cl)Cl>>[NH2:23][CH2:22][CH2:21][C@H:20]([C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([O:13][CH2:12][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[N:19]=1)[OH:24]

Participants

4

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21584172Ammonia methanol dichloromethaneHCID 86694646HCID 86694646, compound

Product 1

HCID 86694645(R)-3-amino-1-(6-(cyclopentylmethoxy)pyridin-2-yl)propan-1-ol

Procedure

LiAlH4 reduction of (R)-3-(6-(cyclopentylmethoxy)pyridin-2-yl)-3-hydroxypropanenitrile following the method described in Example 1 gave after flash chromatography purification (20%-30% 7N NH3/MeOH—CH2Cl2 gradient) Example 33 as a colorless oil. Yield (0.33 g, 24%); 1H NMR (400 MHz, DMSO-d6) δ 7.60 (t, J=7.6 Hz, 1H), 7.00 (d, J=6.8 Hz, 1H), 6.56 (d, J=8.0 Hz, 1H), 4.57-4.51 (m, 1H), 4.10-4.04 (m, 2H), 2.71-2.58 (m, 2H), 2.30-2.02 (m, 1H), 1.82-1.21 (m, 10H); RP-HPLC tR=7.71 min; ESI-MS m/z 251.3 [M+H]+.

Workup

  1. customgave
  2. customYield (0.33 g, 24%)

Sources & evidence

ORD record
ord-8bd40ba846ec4338bb9e8943c17ac1b7
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

Loading…