1-(Diphenylmethyl)azetidin-3-yl methanesulfonate → 3-Amino-1-(diphenylmethyl)azetidine

HRID 366466

反応式

HRID 366466 の反応式
S(O[CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(C)(=O)=O.C1(=O)[NH:27]C(=O)C2=CC=CC=C12.[K]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1>[NH2:27][CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1

参加物

5

反応物 2

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 24194345Phthalimide potassium salt

生成物 1

HCID 57445463-Amino-1-(diphenylmethyl)azetidine

試薬・触媒・溶媒 2

HCID 84716Hexadecyltributylphosphonium bromide触媒HCID 1140Toluene溶媒

実験手順

3-Mesyloxy-1-benzhydrylazetidine (30.32 g, 95.5 mmol), potassium phthalimide (21.59 g, 116.53 mmol) and hexadecyl tributylphosphonium bromide (5.92 g, 11.7 mmol) were added to toluene (600 mL) and the mixture stirred at room temperature overnight. The reaction was then heated at reflux for 3 h. The solid was removed by filtration, washed with EtOAc and the combined organics then washed with H2O. After drying over Na2SO4, the organics were treated with charcoal and then concentrated to an oil. Addition of isopropyl ether induced crystallization of the product (16.37 g, 46%).

後処理

  1. temperatureThe reaction was then heated
  2. temperatureat reflux for 3 h
  3. customThe solid was removed by filtration
  4. washwashed with EtOAc
  5. washthe combined organics then washed with H2O
  6. dry with materialAfter drying over Na2SO4
  7. additionthe organics were treated with charcoal
  8. concentrationconcentrated to an oil
  9. additionAddition of isopropyl ether
  10. customcrystallization of the product (16.37 g, 46%)

出典と根拠

ORDレコード
ord-7df9b80dab8a4c9aa986b75551577bd6
出典データセット
uspto-grants-2000_10
特許番号
US06130217

関連ノート

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