反応式
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:11][CH:10]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:24]S(O)(=O)=O.OOS([O-])=O.[K+].C([O-])(O)=O.[Na+].[OH2:40]>CO>[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([S:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:24])=[O:40])[CH2:9]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1参加物
実験手順
To a solution of 1-(diphenylmethyl)-3-(pentylthio)azetidine (228 mg, 0.70 mmol; which may be prepared as described in Step 2) in methanol (6.3 mL) and water (6.3 mL) was added H2SO4 1N (0.7 mL). The reaction mixture was stirred for 10 minutes, then oxone (1.08 g, 1.75 mmol) was added and the mixture stirred at room temperature for 12 h. A solution of saturated NaHCO3 (5 mL) was added and the mixture extracted with ethyl acetate. The two layers were separated and the organic washed with brine, dried over Na2SO4, filtered and concentrated. The crude was then purified on column chromatography (pentane/EtOAc, 100/0 then 90/10) to give the title product (75 mg, 30%) as a pale yellow oil. The less pure fraction (N-oxide) can be recycled in hydrogenolysis conditions.
後処理
- stirringthe mixture stirred at room temperature for 12 h
- extractionthe mixture extracted with ethyl acetate
- customThe two layers were separated
- washthe organic washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude was then purified on column chromatography (pentane/EtOAc, 100/0
出典と根拠
- ORDレコード
- ord-f630a1a4c82748fa9814874697e5c059
- 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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