反应详情

To a solution of trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (10.0 g, 53.7 mmol) in tetrahydrofuran (540 ml) was added borane-dimethylsulfide complex (6.80 g, 80.6 mmol) at 0-5° C. The cooling bath was removed after 15 minutes and the mixture was stirred for 4 h. The reaction mixture was quenched with methanol (17.2 g, 537 mmol), stirred for 20 minutes and concentrated in vacuo. The residue was triturated in tert-butyl methyl ether (300 ml) and filtrated over a pad of Decalite. The filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate (300 ml) and 1 M aqueous sodium hydroxide solution (100 ml). The layers were separated. The organic layer was washed with one 100 ml-portion of water. The combined aqueous layers were extracted with one 150-ml portion of ethyl acetate. The combined organic layers were washed with one 50 ml-portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (8.75 g, 94.6%) as colorless oil, which can be used without further purification. MS m/e: 172 (M+)

1. customThe cooling bath was removed after 15 minutes
2. stirringstirred for 20 minutes
3. concentrationconcentrated in vacuo
4. customThe residue was triturated in tert-butyl methyl ether (300 ml)
5. filtrationfiltrated over a pad of Decalite
6. concentrationThe filtrate was concentrated in vacuo
7. customThe residue was partitioned between ethyl acetate (300 ml) and 1 M aqueous sodium hydroxide solution (100 ml)
8. customThe layers were separated
9. washThe organic layer was washed with one 100 ml-portion of water
10. extractionThe combined aqueous layers were extracted with one 150-ml portion of ethyl acetate
11. washThe combined organic layers were washed with one 50 ml-portion of brine
12. dry with materialdried over anhydrous sodium sulfate
13. concentrationconcentrated in vacuo