Boron trifluoride etherate → HCID 86701035, 화합물

HRID 1427658노트

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HRID 1427658 반응식
[Si:1]([O:8][CH2:9][CH2:10][C:11]#[N:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:13]([Mg]Br)[CH3:14].B(F)(F)F.CCOCC>CCOCC.C([O-])(C)C.C([O-])(C)C.C([O-])(C)C.C([O-])(C)C.[Ti+4]>[Si:1]([O:8][CH2:9][CH2:10][C:11]1([NH2:12])[CH2:14][CH2:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 8000Boron trifluoride etherateHCID 105355293-((tert-Butyldimethylsilyl)oxy)propanenitrileHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 86701035HCID 86701035, 화합물수율 30%

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 3283Diethyl Ether용매

실험 절차

To a solution of 3-(tert-butyldimethylsilyloxy)propanenitrile (11.1 g, 60 mmol) in Et2O (400 mL) was added titanium tetraisopropanolate (28.9 g, 102 mmol) under N2 atmosphere. Ethylmagnesium bromide (3M in Et2O, 50 mL) was slowly added drop-wise at 0° C. The mixture was stirred at rt for 1 hr. Boron trifluoride etherate (17.0 g, 120 mmol) was slowly added at 0° C. The mixture was stirred at rt for 1 hr. The mixture was quenched with 10% aq. NaOH (300 mL) and then extracted with DCM (3×). The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (gradient elution 5˜50% EtOAc/petroleum ether) to afford 1-(2-(tert-butyldimethylsilyloxy)ethyl)cyclopropanamine (3.9 g, 30%) as a colorless oil. ESI-MS (EI+, m/z): 216.2 [M+H]+.

후처리

  1. customat 0° C
  2. stirringThe mixture was stirred at rt for 1 hr
  3. customThe mixture was quenched with 10% aq. NaOH (300 mL)
  4. extractionextracted with DCM (3×)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (gradient elution 5˜50% EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-df18ee863f9847438b75f6b4d99fc63f
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933233B2

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