Aluminium lithium hydride → HCID 86694665, compound

HRID 63350Notes

Reaction equation

HRID 63350 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH:8]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])[N:20]=1)[CH2:9][CH2:10][NH:11][C:12](=O)OC(C)(C)C.N.CO.C(Cl)Cl>>[CH3:12][NH:11][CH2:10][CH2:9][CH:8]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])[N:20]=1)[OH:7]

Participants

4

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21584172Ammonia methanol dichloromethaneHCID 86694666HCID 86694666, compound

Product 1

HCID 86694665HCID 86694665, compound

Procedure

LiAlH4 reduction of tert-butyl (3-hydroxy-3-(6-((2-propylpentyl)oxy)pyridin-2-yl)propyl)carbamate following the method described in Example 1 gave after flash chromatography purification (30%-40% 7N NH3/MeOH—CH2Cl2 gradient) Example 43 as a colorless oil; Yield (0.04 g, 62%); 1H NMR (400 MHz, DMSO-d6) δ 7.63 (t, J=8.4 Hz, 1H), 7.03 (d, J=8.0 Hz, 1H), 6.62 (d, J=8.0 Hz, 1H), 4.69-4.66 (m, 1H), 4.18-4.16 (m, 2H), 2.76-2.72 (m, 2H), 2.40 (s, 3H), 2.10-1.68 (m, 3H), 1.46-1.26 (m, 8H), 0.96-0.88 (m, 6H); RP-HPLC tR=10.66 min; ESI-MS m/z 295.3 [M+H]+.

Workup

  1. customgave
  2. customYield (0.04 g, 62%)

Sources & evidence

ORD record
ord-28de09a04e584aefb14a1adc9e4ee018
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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