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

HRID 28473

反応式

HRID 28473 の反応式
C(N(CC)CC)C.[CH:8]([N:21]1[CH2:24][CH:23]([OH:25])[CH2:22]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.S(=O)(=O)=O.N1C=CC=CC=1.O>CS(C)=O>[CH:8]([N:21]1[CH2:24][C:23](=[O:25])[CH2:22]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 3304481-(Diphenylmethyl)azetidin-3-ol

生成物 1

HCID 37355581-(Diphenylmethyl)azetidin-3-one収率 170.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

反応条件

温度
10 °C

実験手順

Triethylamine (11.6 ml, 42 mmol) was added to a solution of 1-benzhydryl-azetidin-3-ol (2.0 g, 4.2 mmol) in dimethylsulfoxide (60 mL) at room temperature. The resulting mixture was cooled to 10° C., then pyridine sulfur trioxide (8.64 g, 33.6 mmol) in dimethylsulfoxide was introduced. The mixture was stirred at 10° C. for 1 hour and then for 2 hours at room temperature. The reaction mixture was poured into water (100 mL) and extracted with methylene chloride (3×100 mL). The organic layer was washed with water (3×150 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The crude oil was column chromatographed on silica gel (30% ethyl acetate-hexane). The product-containing fractions were concentrated under vacuum to give 1.7 g (86%) of the title compound as a yellow solid, m.p. 52-54° C.

後処理

  1. waitfor 2 hours at room temperature
  2. extractionextracted with methylene chloride (3×100 mL)
  3. washThe organic layer was washed with water (3×150 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customchromatographed on silica gel (30% ethyl acetate-hexane)
  8. concentrationThe product-containing fractions were concentrated under vacuum

出典と根拠

ORDレコード
ord-2da6b1058eec4ebaa484fa9f3d32c876
出典データセット
uspto-grants-2008_09
特許番号
US07419986B2

関連ノート

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