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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 30763Generated: October 29, 2026

Ethyl Acetate → 4-((1R,2S)-2-(2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethylamino}-1-hydroxypropyl)phenol

https://huagongshe.com/reaction/30763

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantP-HydroxynorephedrineHCID 6931143—
ReactantEthanol, 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-, 1-methanesulfonateHCID 86605506—
SolventDimethylformamideHCID 6228—
Product4-((1R,2S)-2-(2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethylamino}-1-hydroxypropyl)phenolHCID 6854502516.6%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl methanesulfonate (1.20 g) and 4-((1R,2S)-2-amino-1-hydroxypropyl)phenol (1.76 g) in N,N-dimethylformamide (20 mL) was stirred at 80° C. for 5 hrs. Ethyl acetate was added to the reaction mixture. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:n-hexane/ethyl acetate=1/1, methylene chloride/methanol=9/1) to afford the title compound (0.24 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07423185B2
Source datasetuspto-grants-2008_09
ORD IDord-8c7618feeee049eebb73358fc74bc42e
Source noteuspto-grants-2008_09