Water → 1-Benzhydryl-3-(methylsulfonyl)azetidine

HRID 1066899Notes

Reaction equation

HRID 1066899 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10](O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>C(Cl)Cl>[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 155219691-Benzhydryl-3-(methylsulfonyl)azetidineYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of 34 g (0.142 mol) of 1-(diphenylmethyl)-3-hydroxyazetidine in 200 mL of CH2Cl2 was added 30 mL (212 mol) of triethylamine. To the cold mixture a solution of 19.5 g (0.171 mol) of methanesulfonyl chloride in 50 mL of CH2Cl2 was added dropwise. The reaction was stirred at room temperature for 2 h. Water was added and the methylene chloride was removed under vacuo. The product was extracted with ether, the combined extracts were dried over anhydrous sodium sulfate, and filtered to yield 36 g of product. 1H NMR (300 MHz, CDCl3) δ 2.98 (s, 3H), 3.21 (m, 2H), 3.66 (m, 2H), 4.39 (s, 3H), 5.10 (m, 1H), 7.22 (m, 2H), 7.27 (m, 4H), 7.38 (m, 4H).

Workup

  1. customthe methylene chloride was removed under vacuo
  2. extractionThe product was extracted with ether
  3. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ad314b7d23034afb87c9bf7d7a774cfd
Source dataset
uspto-grants-2001_06
Patent number
US06245799B1

Reaction notes

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