Hydrochloric Acid → HCID 136009417, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2-ethyl-4-(tetrahydro-2H-pyran-4-yloxy)cyclopentyl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.145 g, 0.285 mmol) in p-dioxane (6.00 mL) was added an aqueous solution of NaOH (1 N, 1.50 mL, 1.50 mmol). The reaction mixture was stirred at about 55° C. for about 45 min, then cooled to ambient temperature. The reaction mixture was acidified to about pH 2 by the addition of aqueous HCl (1 N, 6 mL). The aqueous layer was extracted with DCM (3×20 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concd to give a brown residue. The crude material was purified by silica gel chromatography using a gradient of 1-10% MeOH in DCM. The stereoisomers were separated using AA (Table 2, Method 32, Rt=15.5 min, or =negative) to give 1-((1S,2R,4S)-2-ethyl-4-(tetrahydro-2H-pyran-4-yloxy)cyclopentyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.048 g, 48%): LC/MS (Table 1, Method a) Rt=1.70 min; MS m/z: 356 (M+H)+.

Provenance & Evidence