4H-Cyclopenta-1,3-dioxol-4-ol, 5-fluoro-3a,6a-dihydro-2,2-dimethyl-6-[(triphenylmethoxy)methyl]-, 4-methanesulfonate, (3aR,4R,6aR)- → 4-Amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-2(1H)-pyrimidinone

Participants

Role	Name	HCID	Charge
Reactant	4H-Cyclopenta-1,3-dioxol-4-ol, 5-fluoro-3a,6a-dihydro-2,2-dimethyl-6-[(triphenylmethoxy)methyl]-, 4-methanesulfonate, (3aR,4R,6aR)-	HCID 90411912	—
Reactant	Cytosine	HCID 178418229	—
Product	4-Amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-2(1H)-pyrimidinone	HCID 11242315	—
Product	(3AS,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol	HCID 90413083	—
Product	HCID 178477758	HCID 178477758	—

Reaction Steps

A reaction using the mesylate 11 and displacement with cytosine under KOtBu/DMSO conditions gave complete conversion, approximately 90% in favour of the desired N1-alkylated product, with the remainder being the O-alkylated product. The two were readily separated by chromatography. After subsequent trityl and acetonide deprotection, compound 13 was afforded with chemical purity of 98.34% area in 50% yield from alcohol 10.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09150520B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-2afca9e78de047f1889ad7feb4607e3d
Source note	uspto-grants-2015_10