1-Pentanethiol → 1-(Diphenylmethyl)-3-(pentylthio)azetidine

HRID 82961

반응식

HRID 82961 반응식
[CH2:1]([SH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[H-].[Na+].CS(O[CH:14]1[CH2:17][N:16]([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15]1)(=O)=O.C([O-])(O)=O.[Na+]>CS(C)=O>[C:19]1([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:16]2[CH2:17][CH:14]([S:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:15]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

6

반응물 4

HCID 80671-PentanethiolHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

생성물 1

HCID 671546441-(Diphenylmethyl)-3-(pentylthio)azetidine수율 96%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
0 °C

실험 절차

To a solution of pentanethiol (248 μL, 2.0 mmol) in DMSO (2.5 mL) at 0° C. under nitrogen was added NaH (60% in oil, 80 mg, 2.0 mmol). The suspension was stirred for 0.5 h at 0° C. then treated with 1-(diphenylmethyl)azetidin-3-yl methanesulfonate (317 mg, 1.0 mmol; which may be prepared as described in Step 1) and the mixture allowed to warm to room temperature overnight. Saturated NaHCO3 (5 mL) was added and the mixture was extracted with diethyl ether. The organic layer was separated from the aqueous and the organic washed with brine, dried over Na2SO4 and concentrated to give the product (312 mg, 96%) as a yellow oil.

후처리

  1. temperatureto warm to room temperature overnight
  2. extractionthe mixture was extracted with diethyl ether
  3. customThe organic layer was separated from the aqueous and the
  4. washorganic washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9db5e2616292487cb7e0fd504a634062
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846711B2

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