4,4,5,5-Tetramethyl-2-{spiro[5.5]undec-2-en-3-yl}-1,3,2-dioxaborolane → 4-Methoxy-1-(4-nitro-3-spiro[5.5]undec-2-en-3-yl-phenyl)piperidine

HRID 2218797Notes

Reaction equation

HRID 2218797 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][CH2:38][C:37]3([CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)[CH2:36][CH:35]=2)O1>>[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][CH2:38][C:37]4([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]4)[CH2:36][CH:35]=3)[CH:14]=2)[CH2:5][CH2:4]1

Participants

3

Reactant 2

HCID 231419414,4,5,5-Tetramethyl-2-{spiro[5.5]undec-2-en-3-yl}-1,3,2-dioxaborolaneHCID 59769425Trifluoromethanesulfonic acid 5-(4-methoxypiperidin-1-yl)-2-nitrophenyl ester

Product 1

HCID 231430114-Methoxy-1-(4-nitro-3-spiro[5.5]undec-2-en-3-yl-phenyl)piperidineYield 111.6%

Procedure

Trifluoromethanesulfonic acid 5-(4-methoxypiperidin-1-yl)-2-nitrophenyl ester (2.0 g, 5.43 mmol) prepared in Example (7c) was used as the starting material. 4,4,5,5-Tetramethyl-2-spiro[5.5]undec-2-en-3-yl-[1,3,2]dioxaborolane (1.65 g, 5.97 mmol) prepared in Example (39b) was used instead of 4-t-butylcyclohex-1-enyl-(4,4,5,5-tetramethyl)-[1,3,2]dioxaborolane for reaction in a manner similar to Example (7e) and treated in a similar manner, to give 2.331 g of the title compound as an orange oil.

Workup

  1. additiontreated in a similar manner

Sources & evidence

ORD record
ord-768e13666180437b93e32ae4b8917137
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Reaction notes

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