Acetone → (1S,5R,6R,7R)-6-[(1E,3R,4R)-3-hydroxy-4-(m-tolyl)-1-pentenyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

Participants

Role	Name	HCID	Charge
Reactant	Acetone	HCID 180	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	Chlorobis((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane	HCID 11131038	—
Reactant	(3aR,4R,5R,6aS)-2-Oxo-4-((R,E)-3-oxo-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate	HCID 67108363	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(1S,5R,6R,7R)-6-[(1E,3R,4R)-3-hydroxy-4-(m-tolyl)-1-pentenyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one	HCID 67108705	440%

Reaction Steps

A solution of enone{(1S,5R,6R,7R)-6-[(1E,4R)-3-oxo-4-(m-tolyl)-1-pentenyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one} (147.0 g) synthesized in Example 3 in THF (1480 mL) was cooled to −40° C., (−)-B-chlorodiisopinocampheylborane (1.7 M hexane solution) (721 mL) was added, and the mixture was stirred under ice-cooling for 20 hr. Acetone (183 mL) was added and the mixture was stirred for 3 hr. Aqueous sodium hydrogen carbonate was added, and the mixture was extracted with t-butyl methyl ether. The extract was dried over magnesium sulfate, and concentrated under reduced pressure to give a crude title compound (649.9 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09034906B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-f4f562a147c34808aaece6283be5b123
Source note	uspto-grants-2015_05