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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 379978Generated: October 25, 2026

Ethyl Acetate → (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid

https://huagongshe.com/reaction/379978

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantTriisopropyl borateHCID 21531—
Reactant(3R,4S)-3-[4-(4-Bromo-phenoxy)-3-(tert-butyl-dimethyl-silanyloxy)-pentyl]-pyridineHCID 57150561—
ReactantHCID 178418306HCID 178418306—
SolventTetrahydrofuranHCID 8028—
Product(1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acidHCID 54020751—

Reaction Steps

Prepared according to the method described in Example 5b) from tert-butyllithium (3.95 ml, 1.7M in hexanes), (3R,4S)-3-[4-(4-bromophenoxy)-3-(tert-butyldimethyl-silanyloxy)pentyl]pyridine (2.52 g, Example 11b)) and tri-isopropylborate (1.68 ml) in tetrahydrofuran (20 ml) to afford the sub-title compound as a foam (1.22 g) after chromatography on silica eluting with ethyl acetate and then ethyl acetate:methanol (4:1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06300352B1
Source datasetuspto-grants-2001_10
ORD IDord-b10f7ea6fca647a99796278aa83dd931
Source noteuspto-grants-2001_10