Borane;tetrahydrofuran → 3-Aminomethyl-6-(tert-butylthio)methyl-pyridine

HRID 1190968Notes

Reaction equation

[C:1]([S:5][CH2:6][C:7]1[N:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[NH2:14][CH2:13][C:10]1[CH:11]=[N:12][C:7]([CH2:6][S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve 6-(tert-butylthio)methyl-pyridine-3-carbonitrile (4.9 g, 23.8 mmol) in anhydrous THF (20 mL) under nitrogen and cool the mixture at 0° C. Add borane-THF complex (71.3 mL, 71.3 mmol, 1M solution in THF). Stir the reaction mixture at room temperature overnight. Pour slowly the reaction mixture into ice-cold 2N aqueous HCl (200 mL) and stir the resulting solution for 4 h. Concentrate in vacuo, take up the resulting solid with a minimum amount of methanol and filter through SCX-2 column eluting with methanol followed by 3N ammonia in methanol to obtain the title compound as a yellow oil (3.8 g, 77%). MS (ES+) m/z: 211 (M+H)+.

Workup

stirringstir the resulting solution for 4 h
concentrationConcentrate in vacuo
filtrationfilter through SCX-2 column
washeluting with methanol

Sources & evidence

ORD record: ord-328a67a8a12d41dc92592be214d64b13
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680091B2

Reaction notes

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