Triethylamine → 1-Benzhydryl-3-methylazetidin-3-yl methanesulfonate

HRID 499070Notes

Reaction equation

Cl.[CH:2]([N:15]1[CH2:18][C:17]([CH3:20])([OH:19])[CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl.O>[CH3:28][S:29]([O:19][C:17]1([CH3:20])[CH2:18][N:15]([CH:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:16]1)(=[O:31])=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

To a slurry of 1-benzhydryl-3-methylazetidin-3-ol hydrochloride (10.00 g, 34.54 mmol) in dichloromethane (80 ml) was added triethylamine (8.00 g, 79.20 mmol) and the mixture cooled to 0° C. Methanesulfonyl chloride (5.20 g, 45.41 mmol) was added dropwise and the reaction mixture was then allowed to warm to room temperature and stirred for 4 hrs. The reaction was diluted with water and dichloromethane and the organic layer was washed further with water, brine then dried (MgSO4) and concentrated to give a pale pink solid. The solid was purified on silica gel eluting with 20% ethyl acetate/petrol to provide the title compound as a white solid (1.69 g, 64%). 1H NMR (CDCl3) 1.92 (3H, s), 3.05 (3H, s), 3.33 (4H, s), 4.42 (1H, s), 7.18-7.20 (2H, m), 7.23-7.30 (4H, m), 7.39-7.52 (4H, m).

Workup

temperatureto warm to room temperature
washthe organic layer was washed further with water, brine
dry with materialthen dried (MgSO4)
concentrationconcentrated
customto give a pale pink solid
customThe solid was purified on silica gel eluting with 20% ethyl acetate/petrol

Sources & evidence

ORD record: ord-e78ad70da2fc4e3ebeb21fed0c2527a9
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767672B2

Reaction notes

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