Dichloromethane → (7R,7aR)-2-Chloro-4-(7-hydroxy-7a-methyl-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-3-methylbenzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	(7R,7aR)-4-[7-(tert-Butyldimethylsilanyloxy)-7a-methyl-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile	HCID 59754338	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(7R,7aR)-2-Chloro-4-(7-hydroxy-7a-methyl-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-3-methylbenzonitrile	HCID 59754283	71.5%

Reaction Conditions

Temperature	0 °C

Reaction Steps

A solution of (7R,7aR)-4-[7-(tert-Butyldimethylsilanyloxy)-7a-methyl-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile (60B) (32 mg, 0.07 mmol) in THF (2 mL) in a plastic vial was cooled to 0° C. HF/pyridine complex (0.12 mL) was added and the reaction was stirred at 0° C. for 1 h and at rt overnight. Saturated aqueous NaHCO3 and CH2Cl2 were added. The layers were separated and the organic layer was concentrated under reduced pressure. The residue was purified via chromatography (silica gel) eluting with 75% EtOAc in hexane to provide the title compound (16 mg). LC/MS m/z 320 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07405234B2
Source dataset	uspto-grants-2008_07
ORD ID	ord-6d60b932aee04e55beb4c909c3f4b740
Source note	uspto-grants-2008_07