Methanesulfonyl chloride → 1-Benzhydryl-3-methylazetidin-3-yl methanesulfonate

HRID 519238Notes

Reaction equation

HRID 519238 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([CH3:19])([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH:1]([N:14]1[CH2:17][C:16]([O:18][S:21]([CH3:20])(=[O:23])=[O:22])([CH3:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 102439891-Benzhydryl-3-methylazetidin-3-ol

Product 1

HCID 100652951-Benzhydryl-3-methylazetidin-3-yl methanesulfonateYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 1-benzhydryl-3-methylazetidin-3-ol (70 g, 276 mmol) and TEA (53.1 g, 525 mmol) in DCM (700 mL) was added drop-wise methanesulfonyl chloride (57 g, 497 mmol). The reaction mixture was stirred for 2 h then filtered and the filter cake was washed with DCM (3×50 mL). The filtrate was washed with water (3×100 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to give methanesulfonic acid 1-benzhydryl-3-methyl-azetidin-3-yl ester (90 g, 98%) as a brown solid, which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz): δ 7.44 (m, 4H), 7.33 (m, 4H), 7.26 (m, 2H), 4.55 (brs, 1H), 3.46 (m, 4H), 3.07 (s, 3H), 1.94 (s, 3H).

Workup

  1. filtrationthen filtered
  2. washthe filter cake was washed with DCM (3×50 mL)
  3. washThe filtrate was washed with water (3×100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f93d10d142704277b972e01cb36e3aa0
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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