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

HRID 2235203ノート

反応式

HRID 2235203 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 160960Diamminetetrachlorotitanate(IV)触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7926f1bffe70403085aeb3fcdc2f5b96
出典データセット
uspto-grants-2010_05
特許番号
US07713979B2

反応ノート

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