Triethylamine → cis(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-yl methanesulfonate

HRID 43918Notes

Reaction equation

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

Participants

Reactant 3

HCID 8471Triethylamine

HCID 31297Methanesulfonyl chloride

HCID 10038631cis(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-ol

Product 1

HCID 10337634cis(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-yl methanesulfonateYield 32.3%

Procedure

The same operation as in Example (234c) was performed using cis(±)-1-(diphenylmethyl)-2-ethylazetidin-3-ol obtained in Example (235b) (769 mg, 2.88 mmol), triethylamine (0.60 mL, 4.32 mmol) and methanesulfonyl chloride (0.29 mL, 3.74 mmol), to obtain 321 mg of the title compound as a pale yellow oily substance (32%).

Sources & evidence

ORD record: ord-3447e6bf48754b2abe9d7b17f20e1699
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

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