反応 #10659

反応方程式

Intermediate 35

trans-4-(N-tert-butoxycarbonylamino)cyclohexanol

1,1′-azobis(N,N-dimethylformamide)

p-anisic acid

tri(n-butyl)phosphine

→

title compound

収率 96.3%

cis-4-methoxybenzoic acid 4-(tert-butoxycarbonylamino)cyclohexyl ester

収率 96.3%

溶媒

ethyl acetate

tetrahydrofuran

反応条件

後処理

1. 1
   温度The reaction mixture was cooled to room temperature
2. 2
   洗浄successively washed with saturated aqueous sodium hydrogencarbonate twice (200 ml each) and 0.1 N aqueous sodium hydroxide (50 ml)
3. 3
   乾燥dried over anhydrous sodium sulfate
4. 4
   その他The solvent was evaporated under reduced pressure
5. 5
   その他the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

実験手順

A solution of Intermediate 35 (21.06 g), 1,1′-azobis(N,N-dimethylformamide) (64.11 g) and p-anisic acid (23.03 g, Tokyo Kasei Kogyo) in tetrahydrofuran (400 ml) was added with tri(n-butyl)phosphine (35.6 ml) at room temperature and stirred at 50° C. for 2.5 hours. The reaction mixture was cooled to room temperature, then added with ethyl acetate (200 ml) and successively washed with saturated aqueous sodium hydrogencarbonate twice (200 ml each) and 0.1 N aqueous sodium hydroxide (50 ml), and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the title compound (32.92 g).

出典