(R)-3-(5-(cyclohexylmethoxy)thiophen-2-yl)-3-hydroxypropanenitrile → HCID 71667841, compound

HRID 63302Notes

Reaction equation

HRID 63302 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[S:13][C:12]([C@H:14]([OH:18])[CH2:15][C:16]#[N:17])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCOCC>[NH2:17][CH2:16][CH2:15][C@H:14]([C:12]1[S:13][C:9]([O:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][CH:11]=1)[OH:18]

Participants

3

Reactant 1

HCID 86694588(R)-3-(5-(cyclohexylmethoxy)thiophen-2-yl)-3-hydroxypropanenitrile

Product 1

HCID 71667841HCID 71667841, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Reduction of (R)-3-(5-(cyclohexylmethoxy)thiophen-2-yl)-3-hydroxypropanenitrile following the method used in Example 1, with the exception that Et2O was used as the solvent, gave after purification by flash chromatography (4%-20% 7N NH3/MeOH—CH2Cl2 gradient) Example 5 as a colorless oil. Yield (0.0185 g, 9%); 1H NMR (400 MHz, CD3OD) δ 6.54-6.59 (m, 1H), 6.00-6.40 (m, 1H), 4.77 (t, J=7.2 Hz, 1H), 3.80 (d, J=5.9 Hz, 2H), 2.86-2.77 (m, 2H), 1.65-1.96 (m, 8H), 1.18-1.36 (m, 3H), 1.00-1.12 (m, 2H); RP-HPLC tR=10.01 min; ESI-MS m/z 252.2 [M−H2O+H]+.

Workup

  1. customgave
  2. customafter purification by flash chromatography (4%-20% 7N NH3/MeOH—CH2Cl2 gradient) Example 5 as a colorless oil
  3. customYield (0.0185 g, 9%)

Sources & evidence

ORD record
ord-47475e55c9c946a388521b4b1f0e84dc
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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