Cyclobutanone → 1-(Cis-2-methyl-cyclohexyl)-pyrrolidin-2-one

HRID 2235203노트

반응식

HRID 2235203 반응식
[N:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:5]1[CH3:10])=[N+]=[N-].[C:11]1(=[O:15])[CH2:14][CH2:13][CH2:12]1>ClCCl.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-]>[CH3:10][C@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@H:4]1[N:1]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15]

참가 물질

5

반응물 2

HCID 14496CyclobutanoneHCID 86624440Cis-1-azido-2-methyl-cyclohexane

생성물 1

HCID 684706881-(Cis-2-methyl-cyclohexyl)-pyrrolidin-2-one수율 36.3%

시약·촉매·용매 2

HCID 160960Diamminetetrachlorotitanate(IV)촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Dissolve cis-1-azido-2-methyl-cyclohexane (Preparation 31) (3.68 g, 26.41 mmol) and cyclobutanone (1.85 g, 26.41 mmol) in dichloromethane (200 mL). Cool the solution to 0° C. and add titanium chloride (15.03 g, 79.23 mmol) under nitrogen. Stir the reaction for 24 hours at room temperature. Add water (200 mL), and extract the aqueous layer with dichloromethane (3×200 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 20-50% of EtOAc/Hexane) to give 1.74 g (36%) of the title compound as a colorless oil.

후처리

  1. customthe reaction for 24 hours at room temperature
  2. extractionAdd water (200 mL), and extract the aqueous layer with dichloromethane (3×200 mL)
  3. dry with materialCombine the organic layers and dry with Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. custompurify by flash column chromatography (silica gel, 20-50% of EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-7926f1bffe70403085aeb3fcdc2f5b96
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713979B2

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