Sodium Hydroxide → (7S,8aS)-7-hydroxy-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

Participants

Reaction Steps

A solution of 0.52 g (1.45 mmol) of (7S,8aS)-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-7-yl benzoate (Example 17) in 50 mL of methanol was treated with 50 mL of 15% aqueous sodium hydroxide and stirred at ambient temperature for 30 minutes. The solent was concentrated by half in vacuo and the residue extracted with chloroform (3×). The combined organic phase was dried (magnesium sulfate), filtered and evaporated Purification by flash silica gel chromatography with 9:1 chloroform:methanol gave 0.25 g (68%) of the title compound. Mp (base) 167-168° C. m/z (MH+) 254.

Provenance & Evidence