Реакция #10659

Уравнение реакции

Intermediate 35

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

1,1′-azobis(N,N-dimethylformamide)

p-anisic acid

tri(n-butyl)phosphine

→

title compound

Выход 96.3%

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

Выход 96.3%

Растворители

ethyl acetate

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was cooled to room temperature
2. 2
   Промывкаsuccessively washed with saturated aqueous sodium hydrogencarbonate twice (200 ml each) and 0.1 N aqueous sodium hydroxide (50 ml)
3. 3
   Сушкаdried over anhydrous sodium sulfate
4. 4
   ДругоеThe solvent was evaporated under reduced pressure
5. 5
   Другоеthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Методика

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).

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