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

HRID 32148Notes

Reaction equation

HRID 32148 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[CH:11][C:12]([N+:23]([O-:25])=[O:24])=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=2)[CH2:5][CH2:4]1.CC1(C)C(C)(C)OB([C:34]2[CH2:39][C:38]([CH3:41])([CH3:40])[CH2:37][C:36]([CH3:43])([CH3:42])[CH:35]=2)O1>COCCOC.O>[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[CH:11][C:12]([N+:23]([O-:25])=[O:24])=[C:13]([C:34]3[CH2:39][C:38]([CH3:41])([CH3:40])[CH2:37][C:36]([CH3:43])([CH3:42])[CH:35]=3)[CH:14]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 231420594,4,5,5-Tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)-1,3,2-dioxaborolaneHCID 59769425Trifluoromethanesulfonic acid 5-(4-methoxypiperidin-1-yl)-2-nitrophenyl ester

Product 1

HCID 231425554-Methoxy-1-[4-nitro-3-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperidine

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

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.

Workup

  1. additiontreated in a similar manner

Sources & evidence

ORD record
ord-d4094e0b7b064768a869efc5abf9c805
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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