Triethylamine → Methanesulfonic acid 1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-piperidin-4-yl ester

HRID 1711734Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:15]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:13]=[CH:12][C:11]=2[O:20][CH:21]([CH3:23])[CH3:22])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[CH:21]([O:20][C:11]1[CH:12]=[CH:13][C:14]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:15][C:10]=1[C:8]([N:5]1[CH2:4][CH2:3][CH:2]([O:1][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:7][CH2:6]1)=[O:9])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.29 mmol (4-hydroxy-piperidin-1-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone in 6 ml dichloromethane at 0° C. were added successively 0.73 mmol triethylamine and 0.35 mmol methanesulfonyl chloride. The reaction mixture was stirred at 0° C. for 20 min and then at RT for 2 h. The reaction mixture was then diluted with dichloromethane, washed with water, and the organic phase dried over sodium sulfate and concentrated in vacuo to afford the title compound as a light brown solid (yield 93%). MS (m/e): 420.1 (M+H+, 100%).

Workup

waitat RT for 2 h
washwashed with water
dry with materialthe organic phase dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5782904fa00043fdaaf90278f63cb018
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790763B2

Reaction notes

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