Sodium Hydroxide → HCID 136359930, compound

Participants

Reaction Conditions

Reaction Steps

To a scalemic mixture enriched in (1R,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl 4-nitrophenyl carbonate (Example #41 Step O, 0.211 g, 0.357 mmol) in 1,4-dioxane (1.5 mL) was added cyclopropylamine (0.102 g, 1.79 mmol). After about 1 h, 1N aqueous sodium hydroxide (1.5 mL, 1.5 mmol) was added and the reaction mixture was heated at about 60° C. for about 30 min then cooled to ambient temperature. The layers were separated and the aqueous layer was extracted with DCM (3×5 mL). The combined organic layers were concd under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-10% MeOH in EtOAc to give (1R,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl cyclopropylcarbamate (0.085 g, 67%): LC/MS (Table 1, Method b) Rt=1.73 min; MS m/z: 355 (M+H)+.

Provenance & Evidence