2-Pyridinesulfonic acid → 1-(Diphenylmethyl)azetidin-3-one

HRID 1437233

反応式

HRID 1437233 の反応式
N1C=CC=CC=1S(O)(=O)=O.[CH:11]([N:24]1[CH2:27][CH:26]([OH:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CS(C)=O.C(N(CC)CC)C>[CH:11]([N:24]1[CH2:27][C:26](=[O:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

5

反応物 2

HCID 948492-Pyridinesulfonic acidHCID 3304481-(Diphenylmethyl)azetidin-3-ol

生成物 1

HCID 37355581-(Diphenylmethyl)azetidin-3-one収率 60%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8471Triethylamine溶媒

実験手順

Under cooling with ice, pyridinesulfonic acid (19.7 g) in dimethyl sulfoxide (84 mL) was added dropwise to 1-benzhydrylazetidin-3-ol (4.79 g) in triethylamine (27.9 mL), and the resultant mixture was stirred at 50° C. for 40 minutes. The reaction mixture was partitioned between ice-water and ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give the title compound as a solid (2.85 g, 60%).

後処理

  1. customThe reaction mixture was partitioned between ice-water and ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate anhydrate
  4. filtrationfollowed by filtration
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-84f5b0b21cc84cbdb8c31f0d43e7a4d2
出典データセット
uspto-grants-2009_11
特許番号
US07622471B2

関連ノート

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