Water → 4-[1-(Diphenylmethyl)azetidin-3-yl]morpholine

HRID 1066064ノート

反応式

HRID 1066064 の反応式
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C(=O)([O-])[O-].[K+].[K+].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C(#N)C>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

生成物 1

HCID 211837864-[1-(Diphenylmethyl)azetidin-3-yl]morpholine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 1-diphenylmethyl-3-methanesulphonyloxyazetidine (see PREPARATION 11 (24.46 g, 7.72 mmol), potassium carbonate (32 g, 3 mol equiv.) and morpholine (7.34 ml, 1.09 mol. equiv.) in acetonitrile (200 ml) was heated under reflux for four hours. The solution was then cooled to room temperature, water (50 ml) added and the mixture concentrated under reduced pressure. The residue was partitioned between ethyl acetate (400 ml) and water (400 ml) and the organic phase separated and washed with water (2×400 ml). The organic phase was dried over magnesium sulphate, filtered and the solvent removed from the filtrate under reduced pressure. The residue was then chromatographed using silica gel eluting with hexane:diethyl ether (1:1, by volume) to give the title compound (16.5 g).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for four hours
  3. concentrationthe mixture concentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate (400 ml) and water (400 ml)
  5. customthe organic phase separated
  6. washwashed with water (2×400 ml)
  7. dry with materialThe organic phase was dried over magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent removed from the filtrate under reduced pressure
  10. customThe residue was then chromatographed

出典と根拠

ORDレコード
ord-9ab57a3b09a94b94b343bdc9bb5e01ed
出典データセット
uspto-grants-2001_06
特許番号
US06242438B1

反応ノート

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