Aluminium lithium hydride → HCID 86694636, compound

HRID 63334Notes

Reaction equation

HRID 63334 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([CH2:14][O:15][C:16]2[N:21]=[C:20]([C@H:22]([OH:26])[CH2:23][C:24]#[N:25])[CH:19]=[CH:18][CH:17]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.N.CO.C(Cl)Cl>>[NH2:25][CH2:24][CH2:23][C@H:22]([C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([O:15][CH2:14][CH:7]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[N:21]=1)[OH:26]

Participants

4

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21584172Ammonia methanol dichloromethaneHCID 86694637HCID 86694637, compound

Product 1

HCID 86694636HCID 86694636, compound

Procedure

LiAlH4 reduction of (R)-3-(6-(cycloheptylmethoxy)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 31 as a colorless oil. Yield (0.11 g, 25%); 1H NMR (400 MHz, DMSO-d6) δ 7.60 (t, J=8.0 Hz, 1H), 7.00 (d, J=6.8 Hz, 1H), 6.67 (d, J=7.6 Hz, 1H), 4.56-4.50 (m, 1H), 4.02-3.98 (m, 2H), 2.72-2.60 (m, 2H), 1.92-1.6 (m, 15H); RP-HPLC tR=9.59 min; ESI-MS m/z 279.2 [M+H]+.

Workup

  1. customgave
  2. customYield (0.11 g, 25%)

Sources & evidence

ORD record
ord-b1ae99f5e34146479146dd21b0db7561
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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