Boron trifluoride etherate → HCID 86701035、化合物

HRID 1430701ノート

反応式

HRID 1430701 の反応式
[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]

参加物

6

反応物 3

HCID 8000Boron trifluoride etherateHCID 105355293-((tert-Butyldimethylsilyl)oxy)propanenitrileHCID 178418443HCID 178418443、化合物

生成物 1

HCID 86701035HCID 86701035、化合物収率 30%

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 3283Diethyl Ether溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-29857b674ef04b8fb7aaed3a3e3dbd58
出典データセット
uspto-grants-2015_01
特許番号
US08940897B2

反応ノート

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