Water → 1-(Diphenylmethyl)azetidin-3-one

HRID 1402027

反応式

HRID 1402027 の反応式
Cl.[C:2]1([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:9]2[CH2:12][CH:11]([OH:13])[CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.S(=O)(=O)=O.O>O1CCCC1.CS(C)=O>[C:14]1([CH:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:9]2[CH2:12][C:11](=[O:13])[CH2:10]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 24682Sulfur trioxideHCID 28017261-benzhydrylazetidin-3-ol Hydrochloride

生成物 1

HCID 37355581-(Diphenylmethyl)azetidin-3-one収率 67%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 1-(diphenylmethyl)azetidin-3-ol hydrochloride salt, (20 g, 72.5 mmol) in tetrahydrofuran (69 ml) and DMSO (173 ml) was added triethylamine (50.5 ml, 362.6 mmol) at 0° C. Then sulphur trioxide:pyridine complex (69 g, 433 mmol) was added portionwise to the reaction mixture over 10 minutes. The resulting yellow solution was stirred at room temperature for 2 hours. Then the reaction mixture was poured in to cold water (173 ml) and extracted with (1:1) ethyl acetate:hexane (5×200 ml). The combined organic layer was washed with water (200 ml), saturated aqueous sodium chloride solution (200 ml), dried over anhydrous sodium sulphate and concentrated in vacuo. Crude product was purified over 100-200 silica gel using 5% v/v ethyl acetate in hexane to get 11.4 g (67%) of the title compound as a white solid.

後処理

  1. extractionextracted with (1:1) ethyl acetate
  2. washThe combined organic layer was washed with water (200 ml), saturated aqueous sodium chloride solution (200 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customCrude product was purified over 100-200 silica gel using 5% v/v ethyl acetate in hexane

出典と根拠

ORDレコード
ord-cb187d3ed9124e9e8ffc4fe06260e09a
出典データセット
uspto-grants-2014_12
特許番号
US08907101B2

関連ノート

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