4-((tert-butoxycarbonylaMino)Methyl)-3-fluorophenylboronic acid synthesis
- Product Name:4-((tert-butoxycarbonylaMino)Methyl)-3-fluorophenylboronic acid
- CAS Number:1374451-80-5
- Molecular formula:C12H17BFNO4
- Molecular Weight:269.08
24424-99-5
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Yield:1374451-80-5 68%
Reaction Conditions:
with N-ethyl-N,N-diisopropylamine in tetrahydrofuran;water at 20; for 2 h;
Steps:
1.b
To a solution of 5 g (29.6 mmol) of 4-aminomethyl-3-fluoro-phenylboronic acid in 30 mL of water and 50 mL of tetrahydrofuran a solution of 6.7 g (30.5 mmol) of ditertbutyl-dicarbonate in 15 mL of tetrahydrofuran was added followed by the addition of 15.5 mL (88.8 mmol) of A^V-diisopropylethylamine. The reaction mixture was stirred at room temperature for 2 h. The pH of the mixture was adjusted to 6 at 0°C by the addition of 2M hydrochloric acid solution and the organic and aqueous phases were separated. The aqueous phase was washed with 3x20 mL of ethyl acetate, the combined organic layers were washed with 10 mL of water and 2x10 mL of brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with hexane and stirred for 2 h. The solid was filtered off and dried to yield 5.44 g (68 %) of the title compound as a yellow oil. MS (EI) 292.1 [M+Na]+.
References:
WO2012/59776,2012,A1 Location in patent:Page/Page column 35-36
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