반응 #10659

반응 방정식

Intermediate 35

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

1,1′-azobis(N,N-dimethylformamide)

p-anisic acid

tri(n-butyl)phosphine

→

title compound

수율 96.3%

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

수율 96.3%

용매

ethyl acetate

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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).

출처