Imidazole → 3-((trans-4-hydroxy-2-(S)-pyrrolidinyl)methoxy)pyridine dihydrochloride

Participants

Role	Name	HCID	Charge
Reactant	Imidazole	HCID 795	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	tert-Butyldimethylsilyl chloride	HCID 28928	—
Reactant	(S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate	HCID 688168	—
Product	3-((trans-4-hydroxy-2-(S)-pyrrolidinyl)methoxy)pyridine dihydrochloride	HCID 67586871	—

Reaction Conditions

Temperature	-23 °C

Reaction Steps

A 7.5 g sample of the compound from step 72a was dissolved in 140 mL of DMF and 2.2 g of imidazole was added. The solution was cooled to -23° C., and 4.84 g of t-butyldimethylsilyl chloride was added and stirred for 1 hour. The volatiles were removed under vacuum, and the residue was purified on a silica gel column, eluting with 1:2 ethyl acetate:hexane to give 8.05 g of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05948793
Source dataset	uspto-grants-1999_09
ORD ID	ord-4b592efb675745b9a995ff7f508638b7
Source note	uspto-grants-1999_09