Acetic Acid → 5,5-Bis-(hydroxymethyl)-1-{4-methoxycarbonyl-2-[(3-pentyl)methylamino]phenyl}pyrrolidin-2-one

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Reaction Steps

A suspension of 1-(2-amino-4-methoxycarbonylphenyl)-5,5-bis-(hydroxymethyl)pyrrolidin-2-one (0.1 g, 0.34 mmol) from Example 6 in 2 mL of dichloromethane was treated with acetic acid (0.1 g, 1.6 mmol), 2-ethylbutyraldehyde (0.065 g, 0.65 mmol) and sodium cyanoborohydride (0.035 g, 0.55 mmol). The resulting mixture was stirred at ambient temperature for 2 h. The reaction mixture was quenched with a saturated sodium bicarbonate solution (2 mL) and the mixture was extracted with ethyl acetate (3×25 mL). The combined organic layers were dried and concentrated to give 0.14 g of crude oil which was purified by chromatography (silica gel; 10% ethanol in ether) to yield 0.115 g (90%) of 5,5-bis-(hydroxymethyl)-1-{4-methoxycarbonyl-2-[(3-pentyl)methylamino]phenyl}pyrrolidin-2-one as white solid, mp 142-143° C.

Provenance & Evidence