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

HRID 2172018

반응식

HRID 2172018 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

HCID 671545941-(Diphenylmethyl)-3-(pentylsulfonyl)azetidine수율 30%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-38c140669b834cb497824707375791fd
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051321B2

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