Water → 1-(Diphenylmethyl)azetidin-3-one

HRID 46359

반응식

HRID 46359 반응식
Cl.[C:2]1([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:9]2[CH2:12][CH:11]([OH:13])[CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.S(=O)(=O)=O.O>O1CCCC1.CS(C)=O>[C:14]1([CH:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:9]2[CH2:12][C:11](=[O:13])[CH2:10]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 24682Sulfur trioxideHCID 28017261-benzhydrylazetidin-3-ol Hydrochloride

생성물 1

HCID 37355581-(Diphenylmethyl)azetidin-3-one수율 67%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 1-(diphenylmethyl)azetidin-3-ol hydrochloride salt, (20 g, 72.5 mmol) in tetrahydrofuran (69 ml) and DMSO (173 ml) was added triethylamine (50.5 ml, 362.6 mmol) at 0° C. Then sulphur trioxide:pyridine complex (69 g, 433 mmol) was added portionwise to the reaction mixture over 10 minutes. The resulting yellow solution was stirred at room temperature for 2 hours. Then the reaction mixture was poured in to cold water (173 ml) and extracted with (1:1) ethyl acetate:hexane (5×200 ml). The combined organic layer was washed with water (200 ml), saturated aqueous sodium chloride solution (200 ml), dried over anhydrous sodium sulphate and concentrated in vacuo. Crude product was purified over 100-200 silica gel using 5% v/v ethyl acetate in hexane to get 11.4 g (67%) of the title compound as a white solid.

후처리

  1. extractionextracted with (1:1) ethyl acetate
  2. washThe combined organic layer was washed with water (200 ml), saturated aqueous sodium chloride solution (200 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customCrude product was purified over 100-200 silica gel using 5% v/v ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-64cdc93dd0b745fbb481ddae2a1ce5a9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541588B2

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