Water → 1-(Diphenylmethyl)-3-(pentylsulfonyl)azetidine

HRID 633918

反応式

HRID 633918 の反応式
[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

7

反応物 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 671546441-(Diphenylmethyl)-3-(pentylthio)azetidine

生成物 1

HCID 671545941-(Diphenylmethyl)-3-(pentylsulfonyl)azetidine収率 30%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

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

  1. stirringthe mixture stirred at room temperature for 12 h
  2. extractionthe mixture extracted with ethyl acetate
  3. customThe two layers were separated
  4. washthe organic washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was then purified on column chromatography (pentane/EtOAc, 100/0

出典と根拠

ORDレコード
ord-d99fc2ffbd124c6c811b142a409c11c5
出典データセット
uspto-grants-2016_04
特許番号
US09321769B2

関連ノート

読み込み中…