反応 #1565606

反応方程式

Diisopropylethylamine

cis-8-ethoxy-10-(4-fluorophenyl)-11-oxa-3-azaspiro[5.5]undecane

3-fluoro-4-(1-hydroxy-1-methyl-ethyl)benzoic acid

EDCI

→

[cis-8-ethoxy-10-(4-fluorophenyl)-11-oxa-3-azaspiro[5.5]undecan-3-yl]-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)phenyl]methanone

収率 23.0%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他The reaction mixture was purified by column chromatography (0-50% EtOAc-Hex)

実験手順

To a solution of cis-8-ethoxy-10-(4-fluorophenyl)-11-oxa-3-azaspiro[5.5]undecane (75 mg, 0.26 mmol) and 3-fluoro-4-(1-hydroxy-1-methyl-ethyl)benzoic acid (56 mg, 0.28 mmol) in CH2Cl2 (1 mL) was added EDCI (54 mg, 0.28 mmol). Diisopropylethylamine (134 μL, 0.767 mmol) was added last. The reaction mixture was allowed to stir at room temperature for 1 hour. The reaction mixture was purified by column chromatography (0-50% EtOAc-Hex) to provide [cis-8-ethoxy-10-(4-fluorophenyl)-11-oxa-3-azaspiro[5.5]undecan-3-yl]-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)phenyl]methanone (28.3 mg). 1H NMR (400 MHz, CDCl3) δ 7.60 (t, J=8.1 Hz, 1H), 7.34 (dd, J=8.5, 5.4 Hz, 2H), 7.14 (dd, J=8.0, 1.6 Hz, 1H), 7.11-7.00 (m, 3H), 4.60-4.30 (m, 2H), 3.77 (br s, 1H), 3.65-3.05 (m, 6H), 2.27 (br s, 2H), 2.23-2.07 (m, 1H), 1.64 (s, 6H), 1.62-1.30 (m, 5H), 1.22 (dd, J=16.6, 9.6 Hz, 3H). ESI-MS m/z calc. 473.24, found 474.5 (M+1)+; Retention time: 1.63 minutes (3 minute run).

出典