(2S,4S)-4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid → (2S,4S)-tert-butyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2-(hydroxymethyl)piperidine-1-carboxylate

Temperatur

0 °C

(2S,4S)-4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (Example 53; 0.250 g, 0.511 mmol) was dissolved in THF (5.0 mL) and the mixture was cooled to 0° C. BH3—SMe2 (0.242 mL, 2.55 mmol) was added and the mixture was warmed to ambient temperature and stirred for 27 hours. The reaction was quenched with MeOH (2 mL) and concentrated. The residue was taken up in EtOAc (30 mL), water (5 mL) and a saturated aqueous Na2CO3 solution (5 mL). The layers were mixed and separated and the aqueous phase washed once with CH2Cl2 (10 mL). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated. During concentration a precipitate formed which was slurried in MeOH, isolated by filtration and washed with Et2O to give 0.119 g (49%) of the desired product as a pale yellow solid.

1. temperaturethe mixture was warmed to ambient temperature
2. customThe reaction was quenched with MeOH (2 mL)
3. concentrationconcentrated
4. additionThe layers were mixed
5. customseparated
6. washthe aqueous phase washed once with CH2Cl2 (10 mL)
7. washThe combined organic phases were washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. concentrationDuring concentration a precipitate
12. customformed which
13. customisolated by filtration
14. washwashed with Et2O

ORD-Eintrag

ord-0b0a3801ec7d40af974297d920baf9e3

Quelldatensatz

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08575145B2