تفاعل #559071

معادلة التفاعل

4-(7-Amino-1-oxo-2-aza-spiro[4.5]dec-2-yl)-piperidine-1-carboxylic acid tert-butyl ester

3-fluorobenzoic acid

BOP

triethylamine

→

title compound

4-[7-(3-Fluoro-benzoylamino)-1-oxo-2-aza-spiro[4.5]dec-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   تركيزThe mixture was concentrated
2. 2
   أخرىthe resulting residue was purified with chromatography (ethyl acetate)

الإجراء التجريبي

4-(7-Amino-1-oxo-2-aza-spiro[4.5]dec-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.20 g, 0.57 mmol), 3-fluorobenzoic acid (0.080 g, 0.56 mmol), BOP (0.252 g, 0.57 mmol), and triethylamine (0.115 g, 1.14 mmol) in methylene chloride (5.0 mL) was stirred at rt overnight. The mixture was concentrated, and the resulting residue was purified with chromatography (ethyl acetate) to afford the title compound which is a mixture of two diastereomers (cis/trans: 3/2; under LC-MS method C, the first peak with RT of 1.47 min was assigned as cis, and the second peak with RT of 1.50 min was assigned as trans.). 1H NMR (400 MHz, CDCl3) δ 8.5 (s, 0.6 H), 7.60-7.68 (m, 1H), 7.36-7.50 (m, 2H), 7.14-7.20 (m, 1H), 5.92 (d, J=6.8 Hz, 0.4 H), 4.55-4.65 (m, 0.4 H), 4.04-4.38 (m, 3.6H), 3.20-3.30 (m, 2H), 2.71-2.86 (m, 2H), 1.28-2.25 (m, 23H). ESI-MS m/z: 474 (M+H)+.

المصدر