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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 69431Generated: October 25, 2026

Hydrogen Bromide → {(R)-1-[2-fluoro-4-(6-hydroxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester

https://huagongshe.com/reaction/69431

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrogen BromideHCID 260—
ReactantDi-tert-butyl dicarbonateHCID 90495—
ReactantSodium BicarbonateHCID 516892—
Reactant{(R)-1-[2-fluoro-4-(6-methoxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl esterHCID 68989909—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
Product{(R)-1-[2-fluoro-4-(6-hydroxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl esterHCID 68991872—

Reaction Steps

According to Method L, {(R)-1-[2-fluoro-4-(6-methoxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester was treated with hydrogen bromide. The raw product (5.5 g) was dissolved in 1,4-dioxan (50 mL) and water (50 mL), sodium hydrogencarbonate (2.6 g) and lastly Boc2O (3.38 g) were added. After 3 hours the 1,4-dioxan was removed in the rotary evaporator and the residue was distributed between water and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. In this way the product was obtained with molecular weight 455.53 (C25H30FN3O4); MS (ESI): 456 (M+H+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822495B2
Source datasetuspto-grants-2014_09
ORD IDord-acb4ebd49b784df997b58c5fd71106eb
Source noteuspto-grants-2014_09