Borane;tetrahydrofuran → 4-Aminomethyl-1-(1-naphthylsulfonyl)piperidine

HRID 2110832Notes

Reaction equation

[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5]1)=O.B.O1CCCC1>O1CCCC1>[NH2:1][CH2:2][CH:4]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-aminocarbonyl-1-(1-naphthylsulfonyl)piperidine (10.6 g, 33.3 mmol) in tetrahydrofuran (200 mL) stirring under argon at room temperature, was added borane-tetrahydrofuran complex (1.5 M in tetrahydrofuran, 67 mL, 100 mmol). The resulting solution was heated to 80° C. for 6 h before the solvent was evaporated under vacuum. The residue was dissolved in 1.0 M aqueous hydrochloric acid (100 mL), and this was washed with diethyl ether (100 mL twice). The aqueous layer was basified to pH 10 with 50% aqueous sodium hydroxide and extracted with dichloromethane (50 mL three times). The combined dichloromethane extracts were dried (anhydrous sodium sulfate) and evaporated under vacuum to obtain 4-aminomethyl-1-(1-naphthylsulfonyl)piperidine (9.1 g, 90% yield).

Workup

customwas evaporated under vacuum
dissolutionThe residue was dissolved in 1.0 M aqueous hydrochloric acid (100 mL)
washthis was washed with diethyl ether (100 mL twice)
extractionextracted with dichloromethane (50 mL three times)
dry with materialThe combined dichloromethane extracts were dried (anhydrous sodium sulfate)
customevaporated under vacuum

Sources & evidence

ORD record: ord-96211a1ab580490d902bc8dbc4f521a4
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517991B2

Reaction notes

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