Sodium Bicarbonate → Acetamide,N-[2-[3,4-dihydro-7-[[[(3R,4R)-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]-3-piperidinyl]oxy]methyl]-1(2H)-quinolinyl]ethyl]-

温度

50 °C

A solution of 0.88 g (1.25 mmol) of (3R,4R)-3-[1-(2-acetylamino-ethyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester in 9 ml of 1,2-dichloroethane was treated with 0.62 g (2.75 mmol, 2.2 equiv.) of anhydrous zinc bromide. The suspension was stirred for 2 h at 50° C. under Argon atmosphere. Subsequently, it was poured into a mixture of 100 ml of ice/water and 10 ml of sat. sodium bicarbonate solution. The aqueous phase was extracted five times with 50 ml of ethyl acetate. The combined organic phases were washed three times with 20 ml of water, dried over magnesium sulphate, evaporated under reduced pressure and dried in a high vacuum. The thus-obtained crude product was purified by chromatography on silica gel using a 100:10:1 v/v/v mixture of dichloromethane/methanol/28% ammonium hydroxide solution as the eluent and yielded 0.36 g (0.60 mmol, 48.0% of theory) of (3R,4R)-N-[2-[7-[4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-3,4-dihydro-2H-quinolin-1-yl]-ethyl]-acetamide as a light yellow oil; MS: 602 (M+H)+.

1. extractionThe aqueous phase was extracted five times with 50 ml of ethyl acetate
2. washThe combined organic phases were washed three times with 20 ml of water
3. dry with materialdried over magnesium sulphate
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 100:10:1 v/v/v mixture of dichloromethane/methanol/28% ammonium hydroxide solution as the eluent

ORDレコード

ord-75a1ef8af52449768aa63d478b2e85e2

出典データセット

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06197959B1