Methanol → HCID 58495525, compound

HRID 1190953Notes

Reaction equation

HRID 1190953 reaction equation
B.C1COCC1.[CH:7]1([S:12][CH2:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1.CO>C1COCC1>[CH:7]1([S:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:18][NH2:19])=[CH:20][CH:21]=2)[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 55027735HCID 55027735, compound

Product 1

HCID 58495525HCID 58495525, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add borane-THF complex (13.6 mL, 13.6 mmol, 1M solution in THF) dropwise to a solution of 4-(cyclopentylthiomethyl)-benzonitrile (1.5 g, 6.8 mmol) in anhydrous THF (8 mL) at room temperature and heat the mixture at reflux overnight. Cool to room temperature, add methanol cautiously and stir vigorously until gas evolution stops. Concentrate in vacuo and purify the crude mixture by SCX chromatography to obtain the title compound (0.86 g, 59%). MS (ES+) m/z: 205 (M-NH3+H)+.

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux overnight
  3. concentrationConcentrate in vacuo
  4. custompurify the crude mixture by SCX chromatography

Sources & evidence

ORD record
ord-fc7ff2b8302d471e986f6f6f2a70cd10
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…