Methanesulfonyl chloride → Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

HRID 2036134Notes

Reaction equation

[OH:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.C(N(C(C)C)C(C)C)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([O:1][CH:2]1[CH2:3][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5]1)(=[O:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of tert-butyl 3-hydroxyazetidine-1-carboxylate A1a (2 g, 11.5 mmol) in dichloromethane (0.5M, 23 mL) is treated with ethyldiisopropylamine (3 mL, 17.5 mmol) and the mixture is cooled to 0° C. Methanesulfonyl chloride (0.99 mL, 12.7 mmol) is then added dropwise and the mixture is allowed to stir at room temperature for 6 hours. The mixture is diluted with dichloromethane, washed with 1M HCl, brine, dried over sodium sulfate and concentrated in vacuo to afford tert-butyl 3-(methylsulfonyloxy)azetidine-1-carboxylate A1b as oil that solidifies upon standing: 1H-NMR (400 MHz, CDCl3) δ=5.25-5.19 (m, 1H), 4.30 (ddd, J=10.4, 6.4, 1.2 Hz, 2H), 4.12 (ddd, J=10.4, 4.0, 1.2 Hz, 2H), 3.09 (s, 3H), 1.46 (s, 9H); MS calcd. for C9H18NO5S ([M+H]+): 252.1, found: 252.2. The product is used without purification.

Workup

washwashed with 1M HCl, brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-518fbc4fc4d24f5a897f72ad47bd8d31
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575168B2

Reaction notes

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