Triethylamine → (1-Benzhydrylazetidin-3-yl)methyl methanesulfonate

HRID 392497Notes

Reaction equation

[C:1]1([CH:7]([N:14]2[CH2:17][CH:16]([CH2:18][OH:19])[CH2:15]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[C:1]1([CH:7]([N:14]2[CH2:17][CH:16]([CH2:18][O:19][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:15]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The title compound from Step B above (1.7 g, 6.72 mmoles) and triethylamine (1.1 g, 10.87 mmoles) were dissolved in CH2Cl2 (20 mL) and the mixture was stirred under nitrogen at 0° C. Methanesulfonylchloride (1.1 g, 9.6 mmoles) was added and the solution was stirred at room temperature for 2 h. The solution was diluted with CH2Cl2 and washed with saturated aqueous sodium bicarbonate, water and dried (MgSO4), filtered and evaporated to dryness to give the title compound (2.32 g, 99%). FABMS (M+1)=332.

Workup

stirringthe solution was stirred at room temperature for 2 h
washwashed with saturated aqueous sodium bicarbonate, water
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-be4167c7ed454984976d4cd793f7cd00
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800636B2

Reaction notes

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