Aluminium lithium hydride → HCID 86694649, compound

HRID 63341Notes

Reaction equation

HRID 63341 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([O:14][C:15]2[N:20]=[C:19]([C@H:21]([OH:25])[CH2:22][C:23]#[N:24])[CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.N.CO.C(Cl)Cl>>[NH2:24][CH2:23][CH2:22][C@H:21]([C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([O:14][CH:7]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[N:20]=1)[OH:25]

Participants

4

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21584172Ammonia methanol dichloromethaneHCID 86694650(R)-3-(6-(cycloheptyloxy)pyridin-2-yl)-3-hydroxypropanenitrile

Product 1

HCID 86694649HCID 86694649, compound

Procedure

LiAlH4 reduction of (R)-3-(6-(cycloheptyloxy)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 34 as a colorless oil. Yield (0.19 g, 14%); 1H NMR (400 MHz, DMSO-d6) δ 7.58 (t, J=8.0 Hz, 1H), 6.97 (d, J=7.2 Hz, 1H), 6.51 (d, J=8.0 Hz, 1H), 5.16-5.08 (m, 1H), 4.56-4.48 (m, 1H), 2.72-2.56 (m, 2H), 1.98-1.36 (m, 14H); RP-HPLC tR=7.98 min; ESI-MS m/z 265.2 [M+H]+.

Workup

  1. customgave
  2. customYield (0.19 g, 14%)

Sources & evidence

ORD record
ord-d81eaeb1af144aa1a19df7b2d3c9efcd
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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