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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 32148Generated: October 28, 2026

4,4,5,5-Tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)-1,3,2-dioxaborolane → 4-Methoxy-1-[4-nitro-3-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperidine

https://huagongshe.com/reaction/32148

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4,4,5,5-Tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)-1,3,2-dioxaborolaneHCID 23142059—
ReactantTrifluoromethanesulfonic acid 5-(4-methoxypiperidin-1-yl)-2-nitrophenyl esterHCID 59769425—
SolventWater 1,2-dimethoxyethaneHCID 18180031—
Product4-Methoxy-1-[4-nitro-3-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperidineHCID 23142555—

Reaction Steps

Trifluoromethanesulfonic acid 5-(4-methoxypiperidin-1-yl)-2-nitrophenyl ester (3 g, 7.81 mmol) prepared in Example (7c) was used as the starting material. 4,4,5,5-Tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-enyl)-[1,3,2]dioxaborolane prepared in Example (4b) was used instead of 4-t-butylcyclohex-1-enyl-(4,4,5,5-tetramethyl)-[1,3,2]dioxaborolane, and a mixed solvent of 1,2-dimethoxyethane-water was used as the solvent, for reaction in a manner similar to Example (7e) and treated in a similar manner, to give 2.89 g of the title compound as a yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07425554B2
Source datasetuspto-grants-2008_09
ORD IDord-d4094e0b7b064768a869efc5abf9c805
Source noteuspto-grants-2008_09