(3R,7aR)-3-(1,1-Dimethylethyl)-7a-ethenyltetrahydro-1-hydroxy-3H,5H-pyrrolo[1,2-c]oxazol-5-one

To a 500 mL three-necked flask (1) equipped with an agitator, thermometer, and a nitrogen inlet were added XVI (30.0 g, 132 mmol) and THF (300 mL). After cooling mixture to −20° C., lithium tri(t-butoxy)aluminum hydride (1 M THF; 162 mL) was added over 2 h while maintaining the temperature around −20° C. Temperature was then raised to 0° C. over 12 h. The reaction is quenched with the addition of EtOAc (12.0 mL) over 30 min, followed by agitation for 30 min at 0° C., and then slow addition of glacial AcOH (12.0 mL) over 30 min. To another 1-L three-necked flask (2) equipped with an agitator, thermometer, and a nitrogen inlet were added finely ground sodium sulfate decahydrate (30 g, 93 mol) and THF (150 mL) at 0° C. The reaction mixture in flask (1) was slowly transferred to flask (2) containing the sodium sulfate decahydrate solution while maintaining the temperature at 0° C. The temperature of flask (2) was raised over a 1 h period and agitated for 1 h at 20° C. The contents of flask (2) were filtered, the wet cake was washed three times with THF (180 mL, 120 mL, and then 120 mL), and the filtrates were combined and concentrated in vacuum to 60 mL. To a 1000 mL three-necked flask (3) equipped with an agitator, thermometer, and a nitrogen inlet was added water (300 mL). The mixture from flask (2) was cooled to 5° C. and then added to the water with high agitation over a 2 h period, whereupon the product precipitated. The slurry was concentrated in vacuum to 450 mL and the solid was isolated via filtration. The wet cake was dried at 50° C. for 12 h to afford 25.1 g of the compound of formula H as a white/off white solid in 83percent yield. Mp 88° C.

Molecular Weight:225.28
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:225.13649347
Monoisotopic Mass:225.13649347
Topological Polar Surface Area:49.8
Heavy Atom Count:16
Complexity:334
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes