Diisopropylethylamine → tert-butyl (2S,6R,8aR)-3-oxo-6-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-octahydroindolizin-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(2S)-6-amino-3-oxooctahydroindolizin-2-ylcarbamate 127.2 (0.913 g, 3.39 mmol) in DMF (25 ml) and was added 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (100 mg (3.4 mmole) 127.a and DIEA (1.18 mL (6.78 mmole) at solution was heated 90° C. for 24 hr. After cooling to room temperature, the mixture was diluted with H2O and washed with EtOAc (2×). The combined organics were washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo, absorbing onto 6 g silica gel. Purification by flash column chromatography (ISCO 40 g SiO2, 50% EtOAc/hexanes then gradient to 100% EtOAc/hexanes) yielded 0.52 g of tert-butyl (2S,6S,8aS)-3-oxo-6-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)octahydroindolizin-2-ylcarbamate 127.3 and 0.55 g of tert-butyl (2S,6R,8 aR)-3-oxo-6-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)octahydroindolizin-2-ylcarbamate 127.4.

Provenance & Evidence