反応 #1565613

反応方程式

Sodium borohydride

3-(4-isopropoxy-3-methoxy-benzoyl)-10-phenyl-11-oxa-3-azaspiro[5.5]undecan-8-one

trichlorocerium

→

[cis-8-hydroxy-10-phenyl-11-oxa-3-azaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methoxy-phenyl)methanone

[trans-8-hydroxy-10-phenyl-11-oxa-3-azaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methoxy-phenyl)methanone

溶媒

MeOH

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 20 minutes
2. 2
   その他The reaction was quenched with water
3. 3
   抽出extracted with ethyl acetate (2×)
4. 4
   洗浄The combined organic layers were washed with brine
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated to dryness
8. 8
   その他The crude material was purified by column chromatography (40-60% ethyl acetate-Hex)

実験手順

To a solution of 3-(4-isopropoxy-3-methoxy-benzoyl)-10-phenyl-11-oxa-3-azaspiro[5.5]undecan-8-one (4.50 g, 10.3 mmol) in MeOH (110 mL) was added trichlorocerium (2.79 g, 11.3 mmol). The mixture was stirred at room temperature for 5 minutes. Sodium borohydride (467 mg, 12.4 mmol) was added. The mixture was stirred at room temperature for 20 minutes. The reaction was quenched with water and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to dryness. The crude material was purified by column chromatography (40-60% ethyl acetate-Hex) to provide [cis-8-hydroxy-10-phenyl-11-oxa-3-azaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methoxy-phenyl)methanone (1.5 g) and [trans-8-hydroxy-10-phenyl-11-oxa-3-azaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methoxy-phenyl)methanone (1.3 g). cis-isomer: 1H NMR (400 MHz, CDCl3) δ 7.43-7.33 (m, 4H), 7.33-7.27 (m, 1H), 6.96 (d, J=1.6 Hz, 1H), 6.95-6.90 (m, 1H), 6.86 (d, J=8.2 Hz, 1H), 4.65-4.48 (m, 2H), 4.23-4.05 (m, 2H), 3.95-3.75 (m, 1H), 3.85 (s, 3H), 3.49 (s, 1H), 3.20 (s, 1H), 2.25 (dd, J=20.6, 8.4 Hz, 2H), 1.98 (dd, J=12.5, 2.9 Hz, 1H), 1.73 (s, 2H), 1.62-1.40 (m, 3H), 1.37 (t, J=6.0 Hz, 6H). ESI-MS m/z calc. 439.24, found 440.4 (M+1)+; Retention time: 1.49 minutes (3 minute run). trans-isomer 1H NMR (400 MHz, CDCl3) δ 7.43-7.38 (m, 2H), 7.39-7.33 (m, 2H), 7.31-7.24 (m, 1H), 6.96 (d, J=1.7 Hz, 1H), 6.92 (dd, J=8.2, 1.8 Hz, 1H), 6.85 (d, J=8.2 Hz, 1H), 4.97 (d, J=11.2 Hz, 1H), 4.55 (dt, J=12.2, 6.1 Hz, 1H), 4.44-4.32 (m, 1H), 4.05-3.75 (m, 2H), 3.85 (s, 3H), 3.49 (s, 1H), 3.24 (s, 1H), 2.77 (dd, J=25.2, 13.7 Hz, 1H), 1.96 (d, J=13.4 Hz, 1H), 1.84-1.70 (m, 2H), 1.70-1.54 (m, 5H), 1.37 (d, J=6.1 Hz, 6H). ESI-MS m/z calc. 439.24, found 440.2 (M+1)+; Retention time: 1.61 minutes (3 minute run).

出典