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

HRID 83058

反応式

HRID 83058 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>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

4

反応物 2

HCID 8471TriethylamineHCID 3304481-(Diphenylmethyl)azetidin-3-ol

生成物 1

HCID 37355581-(Diphenylmethyl)azetidin-3-one

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 (29.1 mL, 209 mmol) and a solution of sulphur trioxide pyridine complex (21.3 g, 134 mmol) in DMSO (100 mL) were added at 10° C. to a solution of 1-benzhydrylazetidin-3-ol (5.0 g, 20.9 mmol) in DMSO (60 mL). The resulting mixture was stirred at 10° C. for 45 minutes, then at room temperature for 4 hours, subsequently quenched by pouring onto crushed ice (˜200 g) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water (400 mL) and brine (400 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (80:20 to 70:30) as eluent. The title product was obtained as a yellowish solid (4.35 g, 88%).

後処理

  1. waitat room temperature for 4 hours
  2. customsubsequently quenched
  3. additionby pouring
  4. customonto crushed ice (˜200 g)
  5. extractionextracted with ethyl acetate (3×200 mL)
  6. washThe combined organic layers were washed with water (400 mL) and brine (400 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-68343e2ae16c4375b0c07b2b3eeb54c0
出典データセット
uspto-grants-2014_09
特許番号
US08846711B2

関連ノート

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