Boron trifluoride etherate → HCID 86701035, 화합물

HRID 1855192노트

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HRID 1855192 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 10535529HCID 10535529, 화합물HCID 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-butyldim ethylsilyloxy)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-0a0d34c616334a6086cc8659b6d01b05
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962843B2

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