Triethylamine → Tert-butyl 4-(3-((methylsulfonyl)oxy)propyl)piperidine-1-carboxylate

HRID 1978340Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(OCC)C.O>[S:26]([O:17][CH2:16][CH2:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1)(=[O:28])(=[O:27])[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4.87 g (20.0 mM) of 3-(1-tert-butoxycarbonyl-4-piperidyl)-1-propanol and 5.6 ml (40.0 mM) of triethylamine in 50 ml of diethyl ether was added 1.86 ml (24.0 mM) of methanesulfonyl chloride at 0° C. and the mixture was stirred at 0° C. for 30 minutes. This reaction mixture was then poured in iced water and extracted with ether. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4 and the solvent was distilled off under reduced pressure to provide 3-(1-tert-butoxycarbonyl-4-piperidyl)-1-propyl mesylate. To a solution of the above mesylate in 100 ml of N,N-dimethylformamide was added 3.70 g (20.0 mM) of potassium phthalimide and the mixture was heated at 100° C. for 90 minutes. After cooling to room temperature, this reaction mixture was poured in iced water and the resulting precipitate was collected by filtration, rinsed with water, and dried in vacuo to provide the title compound as white solid (20.24 g, 90%).

Workup

extractionextracted with ether
washThe organic layer was washed with saturated aqueous solution of sodium chloride
dry with materialdried over MgSO4
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-7eb4631a92b64678a39dc4e718228e27
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235731B1

Reaction notes

Loading…