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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1866511Generated: November 2, 2026

3-{2-[(2R)-2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyldimethyl-silanyloxy)ethylamino]-2-methylpropyl}benzoic acid methyl ester → 3-(2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid methyl ester

https://huagongshe.com/reaction/1866511

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-{2-[(2R)-2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyldimethyl-silanyloxy)ethylamino]-2-methylpropyl}benzoic acid methyl esterHCID 57978228—
CatalystPalladiumHCID 23938—
SolventMethanolHCID 887—
Product3-(2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid methyl esterHCID 69024800—

Reaction Steps

3-{2-[(2R)-2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyldimethyl-silanyloxy)ethylamino]-2-methylpropyl}benzoic acid methyl ester (Preparation 35) (2.12 g, 3.70 mmol) and palladium-on-carbon (10%, 300 mg) in methanol (50 ml) were hydrogenated at room temperature and 60 psi for 18 hours. The reaction mixture was filtered through arbocel and the filtrate concentrated in vacuo, the residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 by volume) to furnish the title compound, this material was taken up in diethylether and evaporated (×3) to yield a white foam (1.50 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07629358B2
Source datasetuspto-grants-2009_12
ORD IDord-10f24f8a6028464fa839fe5c6d49600b
Source noteuspto-grants-2009_12