Water → 1-Boc-4-(aminomethyl)piperidine

Reaction equation

[N:1]([CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

Participants

Procedure

Tertiary butyl 4-(azidomethyl)piperidine-1-carboxylate (30 g, 124.8 mmol) was dissolved in tetrahydrofuran (300 mL), and triphenylphosphine (39.3 g, 149.8 mmol) was added thereto, followed by stirring under reflux for 2 hours. Water (120 mL) was added thereto, followed by stirring under reflux for another 3 hours and concentration under reduced pressure. The resulting residue was extracted with ethyl acetate and a 1N hydrochloride solution, and the aqueous layer was neutralized with a 2N sodium hydroxide solution, followed by re-extraction with dichloromethane. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the title compound (21.16 g, 79%).