Methanesulfonyl chloride → 1,1-Dimethylethyl 4-[[(methylsulfonyl)oxy]-2-pyridinylmethyl]-1-piperidinecarboxylate

HRID 1426160Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 4-(hydroxy(pyridin-2-yl)methyl)piperidine-1-carboxylate (Prepared in Example 124; 8.00 g, 27.4 mmol) and TEA (11.4 ml, 82.1 mmol) were combined and cooled to 0° C. Methanesulfonyl chloride (2.65 ml, 34.2 mmol) was added and the reaction mixture was stirred at ambient temperature for 18 hours. Water was added and the reaction mixture was extracted with dichloromethane. The organic layer was dried, filtered, and concentrated to give tert-butyl 4-((methylsulfonyloxy)(pyridin-2-yl)methyl)piperidine-1-carboxylate (9.9 g, 97.7% yield). 1H NMR (DMSO-d6) δ 10.88 (bs, 1H), 8.49 (d, 1H), 8.35 (d, 1H), 7.95 (m, 1H), 7.75 (s, 1H), 7.65 (t, 1H), 7.57 (d, 2H), 7.42 (m, 3H), 7.36 (m, 1H), 7.31 (s, 1H), 7.21 (m, 1H), 7.14 (d, 1H), 5.23 (s, 2H), 4.19 (d, 1H), 3.98 (m, 1H), 3.84 (m, 1H), 2.14 (m, 2H), 1.37 (m, 10H), 1.20 (m, 3H), 1.01 (m, 1H).

Workup

extractionthe reaction mixture was extracted with dichloromethane
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-bb4d1726587c4f448220e41d058d44ef
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933077B2

Reaction notes

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