Boron trifluoride etherate → HCID 86701035, compound
Reaction equation
[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]Participants
Procedure
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]+.
Workup
- customat 0° C
- stirringThe mixture was stirred at rt for 1 hr
- customThe mixture was quenched with 10% aq. NaOH (300 mL)
- extractionextracted with DCM (3×)
- dry with materialThe combined organic layer was dried over Na2SO4
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (gradient elution 5˜50% EtOAc/petroleum ether)
Sources & evidence
- ORD record
- ord-df18ee863f9847438b75f6b4d99fc63f
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933233B2
Reaction notes
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