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

HRID 366466

반응식

HRID 366466 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 57445463-Amino-1-(diphenylmethyl)azetidine

시약·촉매·용매 2

HCID 84716Hexadecyltributylphosphonium bromide촉매HCID 1140Toluene용매

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-7df9b80dab8a4c9aa986b75551577bd6
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130217

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