Hydrazine → ((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(6-(trifluoromethyl)-2H-benzo[e][1,3]oxazin-3(4H)-yl)methanone

Participants

Role	Name	HCID	Charge
Reactant	Hydrazine	HCID 9321	—
Reactant	2-((3aS,5S,6aR)-3a-(6-(trifluoromethyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine-3-carbonyl)hexahydro-2H-cyclopenta[b]furan-5-yl)isoindoline-1,3-dione	HCID 86708155	—
Solvent	Ethanol	HCID 702	—
Product	((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(6-(trifluoromethyl)-2H-benzo[e][1,3]oxazin-3(4H)-yl)methanone	HCID 86708156	—

Reaction Steps

A solution of the product of Step D (5.39 g, 11.1 mmol, 1 eq) and hydrazine (7.1 mL, 222 mmol, 20 eq) in ethanol (60 mL) was stirred at rt 18 hours. The white solid was filtered, washed with methanol and DCM, and the filtrates concentrated. Saturated NaHCO3 was added, the aqueous extracted with DCM, the organics combined, dried over MgSO4 and concentrated to afford the product of Step E. Calculated for C17H19F3N2O3: 357.1 (M+1). found: 357.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09150532B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-aaf9f4cce2fe425cb21e4075fdf669df
Source note	uspto-grants-2015_10