تفاعل #10659

معادلة التفاعل

Intermediate 35

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

1,1′-azobis(N,N-dimethylformamide)

p-anisic acid

tri(n-butyl)phosphine

→

title compound

المردود 96.3%

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

المردود 96.3%

المذيبات

ethyl acetate

tetrahydrofuran

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر