Methanesulfonyl chloride → HCID 86727621, compound

HRID 519209Notes

Reaction equation

HRID 519209 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([CH3:19])(O)[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.CS([Cl:24])(=O)=O>C(Cl)Cl>[CH:1]([N:14]1[CH2:17][C:16]([Cl:24])([CH3:19])[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

Participants

4

Reactant 2

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

Product 1

HCID 86727621HCID 86727621, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of TEA (30 g, 296 mmol) and 1-benzhydryl-3-methyl-azetidin-3-ol (30 g, 118 mmol) in DCM (300 mL) at 0° C. was added a solution of methanesulfonyl chloride (20.49 g, 179 mmol) in DCM (15 mL) keeping the internal temperature below 5° C. The mixture was stirred at ambient temperature for 20 h and quenched by addition of water (50 mL). The organic phase was separated, dried over anhydrous Na2SO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 0% EtOAc to 50% EtOAc in petroleum ether) to give 1-benzhydryl-3-chloro-3-methyl-azetidine (7 g, 22%): 1H NMR (CDCl3, 400 MHz): δ7.42-7.45 (m, 4H), 7.27-7.31 (m, 4H), 7.18-7.23 (m, 2H), 4.48 (s, 1H), 3.38-3.44 (m, 4H), 1.87 (s, 3H) and methanesulfonic acid 1-benzhydryl-3-methyl-azetidin-3-yl ester (16 g, 41%). 1H NMR (CDCl3, 400 MHz): δ7.40-7.37 (m, 4H), 7.20-7.28 (m, 4H), 7.16-7.20 (m, 2H), 4.42 (s, 1H), 3.33 (s, 4H), 3.02 (s, 3H), 1.90 (s, 3H).

Workup

  1. customthe internal temperature below 5° C
  2. customquenched by addition of water (50 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (eluting with 0% EtOAc to 50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-90f2527e72364011813b436f145aa88d
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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