Methanesulfonyl chloride → tert-Butyl 4-[(6-{[(methylsulfonyl)oxy]methyl}pyridin-2-yl)oxy]piperidine-1-carboxylate

HRID 2239362Notes

Reaction equation

[OH:1][CH2:2][C:3]1[N:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:23][S:24]([O:1][CH2:2][C:3]1[N:8]=[C:7]([O:9][CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)[CH:6]=[CH:5][CH:4]=1)(=[O:26])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 4-{[6-(hydroxymethyl)pyridin-2-yl]oxy}piperidine-1-carboxylate (0.34 g, 1.10 mmol) and methanesulfonyl chloride (0.13 mL, 1.64 mmol) were dissolved in DCM (15 mL) and stirred at 0° C. (ice bath). DIPEA (0.57 mL, 3.29 mmol) was added to the reaction mixture and stirred for 2 hours. The resulting mixture washed with water (2×15 mL), dried over a phase separator, concentrated in vacuo and was used directly in the next step.

Workup

stirringstirred for 2 hours
washThe resulting mixture washed with water (2×15 mL)
customdried over a phase separator
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-dadc3e871b554646a860ff280b47c92b
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723331B2

Reaction notes

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