反应详情

温度

0 °C

To an ice-cooled solution of 0.250 g (0.379 mmol) (3R,4R)-3-[1-(2-amino-ethyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester [example 15(b)] and 0.049 g (0.493 mmol, 1.3 equiv.) triethylamine in 5 ml of dichloromethane was added dropwise at 0° C. 0.047 g (0.417 mmol, 1.1 equiv.) methanesulfonyl chloride. After stirring for 30 min at 0° C., the reaction mixture was poured into 50 ml of an ice/water mixture and extracted three times with 50 ml of ethyl acetate. The combined organic phases were washed twice with 25 ml of water, evaporated under reduced pressure and dried in a high vacuum. The thus obtained crude product was purified by chromatography on silica gel using a 1:2 v/v mixture of hexane and ethyl acetate as eluent to yield 0.247 g (0.335 mmol, 88.3% of theory) of (3R,4R)-3-[1-(2-methanesulfonylamino-ethyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester as a light yellow oil; MS: 736 (M+H)+.

1. additionwas added dropwise at 0° C
2. extractionextracted three times with 50 ml of ethyl acetate
3. washThe combined organic phases were washed twice with 25 ml of water
4. customevaporated under reduced pressure
5. customdried in a high vacuum
6. customThe thus obtained crude product
7. customwas purified by chromatography on silica gel using
8. additiona 1:2 v/v mixture of hexane and ethyl acetate as eluent