Quinagolide

Quinagolide (INNTooltip International nonproprietary name, BANTooltip British Approved Name), sold under the brand name Norprolac, is a selective dopamine D2 receptor agonist which is used to reduce elevated levels of prolactin (hyperprolactinemia).

Transformation of the ester (13) into the amine (15) is accomplished by a Curtius rearrangement in which an acyl hydrazide is treated with nitrosyl chloride.

Birch reduction of (5) leads first to (6) which on acid work-up gives the imine (7), which is reduced with sodium borohydride to yield (8).

[7][8][9] Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.

(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)