Borane → (R)-3-amino-1-(6-(2-ethylbutoxy)pyridin-2-yl)propan-1-ol

HRID 63332Notes

Reaction equation

HRID 63332 reaction equation
B.[CH2:2]([CH:4]([CH2:18][CH3:19])[CH2:5][O:6][C:7]1[N:12]=[C:11]([C:13](=[O:17])[CH2:14][C:15]#[N:16])[CH:10]=[CH:9][CH:8]=1)[CH3:3].N.CO.C(Cl)Cl>>[NH2:16][CH2:15][CH2:14][C@H:13]([C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([O:6][CH2:5][CH:4]([CH2:18][CH3:19])[CH2:2][CH3:3])[N:12]=1)[OH:17]

Participants

4

Reactant 3

HCID 6331BoraneHCID 21584172Ammonia methanol dichloromethaneHCID 86694631HCID 86694631, compound

Product 1

HCID 86694633(R)-3-amino-1-(6-(2-ethylbutoxy)pyridin-2-yl)propan-1-ol

Procedure

Borane reduction of 3-(6-(2-ethylbutoxy)pyridin-2-yl)-3-oxopropanenitrile following the method described in Example 6 gave after flash chromatography purification (25%-30% 7N NH3/MeOH—CH2Cl2 gradient) Example 30 as a colorless oil. Yield (0.11 g, 25%); 1H NMR (400 MHz, DMSO-d6) δ 7.61 (t, J=7.6 Hz, 1H), 7.0 (d, J=7.6 Hz, 1H), 6.57 (d, J=8.4 Hz, 1H), 4.57-4.50 (m, 1H), 4.15-4.06 (m, 2H), 2.70-2.58 (m, 2H), 1.84-1.76 (m, 1H), 1.64-1.52 (m, 2H), 1.42-1.28 (m, 4H), 0.85 (t, J=7.2 Hz, 6H); RP-HPLC tR=8.51 min; ESI-MS m/z 253.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-ab4394e141a34b349966d56dd2dd5b42
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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