反应详情

To a stirred solution of N-(2-(6-(cyclopropylmethoxy)-3-formylquinolin-2-ylamino)ethyl)acetamide SLA 47092 (0.35 g, 1.1 mmol) in THF (10 mL) in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.04 g, 1.1 mmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 1 N aq. HCl solution. After stirring for 15 min at RT, the mixture was basified to pH=9 with a 2 N aq. NaOH solution. THF was removed at 40° C. under vacuum and the residue was extracted with CH2Cl2 (200 mL), washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated under vacuum, to give N-(2-(6-(cyclopropylmethoxy)-3-(hydroxymethyl)quinolin-2-ylamino)ethyl)acetamide SLA 47096A as a yellow oil (0.39 g, quant. yield).

1. temperaturethen cooled in an ice bath
2. custombefore quenching by addition of a 1 N aq. HCl solution
3. stirringAfter stirring for 15 min at RT
4. customTHF was removed at 40° C. under vacuum
5. extractionthe residue was extracted with CH2Cl2 (200 mL)
6. washwashed with brine (20 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under vacuum