Acetic Acid → Methyl (5Z,13E,15R)-9beta-chloro-11alpha,15-dihydroxy-16,16-dimethylprosta-5,13-dien-1-oate

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	Cerium(III) chloride	HCID 24636	—
Reactant	Sodium borohydride	HCID 4311764	—
Reactant	(+/-)-(Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(E)-4,4-dimethyl-3-oxo-1-octenyl]-3-hydroxy-cyclopentyl}-5-heptenic acid methyl ester heptenic acid methyl ester	HCID 86742756	—
Solvent	Methanol	HCID 887	—
Product	Methyl (5Z,13E,15R)-9beta-chloro-11alpha,15-dihydroxy-16,16-dimethylprosta-5,13-dien-1-oate	HCID 13853250	—

Reaction Steps

A solution of 600 mg of IX in 25 ml of methanol is mixed with 60 mg of cerium(III) chloride with stirring and then 500 mg of sodium borohydride is added at -40° C. After 1 hour, thin-film chromatography checking shows a complete reduction. It is installed with 1 ml of glacial acetic acid, concentrated by evaporation in a vacuum, diluted with water and extracted several times with dichloromethane. The combined organic phases are washed with sodium bicarbonate solution and salt water, dried over magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with dichloromethane/1-10% acetane. First 280 mg of XI is eluted as nonpolar component and then 295 mg of the desired epimer X, both as colorless oils.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04806668
Source dataset	uspto-grants-1989_02
ORD ID	ord-978bc160c1ac428b878612ee98813bfa
Source note	uspto-grants-1989_02