Reacción #302983

Ecuación de reacción

{(3R,6S)-6-[(1S)-1-hydroxy-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester

DIPEA

Pyr

→

solid

Rendimiento 74.6%

{(3R,6S)-6-[2-(6-methoxy-[1,5]naphthyridin-4-yl)-acetyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester

Rendimiento 74.6%

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe volatiles were removed under reduced pressure and water (20 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   FiltraciónThe resulting precipitate was filtered
4. 4
   Otrofurther dried under HV

Procedimiento

To a solution of {(3R,6S)-6-[(1S)-1-hydroxy-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (prepared as described in WO 2006/032466, 0.78 g, 1.73 mmol) cooled to −10° C. was added dropwise DIPEA (1.03 mL, 5.90 mmol). A solution of Pyr.SO3 (0.684 g, 48%, 1.1 eq.) in DMSO (2 mL) was added dropwise. The reaction mixture was stirred for 1 h 45 at 0° C. The volatiles were removed under reduced pressure and water (20 mL) was added. The resulting precipitate was filtered and further dried under HV to give a yellow solid (0.518 g, 66% yield).

Fuente