HCID 66768828, compound → 9-Borabicyclo(3.3.1)nonane

HRID 2360476Notes

Reaction equation

HRID 2360476 reaction equation
[CH:1]12[B:9]([CH2:10][CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2>O1CCCC1>[CH2:10]=[C:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.[CH:5]12[BH:9][CH:1]([CH2:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2

Participants

4

Reactant 1

HCID 66768828HCID 66768828, compound

Product 2

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 27568081-Boc-4-Methylenepiperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

For this the compounds of general formula XV are reacted with tert.-butyl 4-(9-borabicyclo[3.3.1]nonan-9-ylmethyl)-piperidine-1-carboxylate (obtained from the reaction of tert-butyl 4-methylene-piperidine-1-carboxylate with 9-bora-bicyclo[3.3.1]nonane in tetrahydrofuran at reflux temperature) or tert-butyl 4-(9-bora-bicyclo[3.3.1]non-9-ylmethyl)-azepan-1-carboxylate (obtained from the reaction of tert-butyl 4-methylene-azepan-1-carboxylate with 9-bora-bicyclo[3.3.1]nonane in tetrahydrofuran at reflux temperature) in the presence of a catalyst such as [1,1′-bis(diphenylphosphino)ferrocene]-palladium-II-dichloride-dichloromethane complex, bis-tri-tert.-butylphosphine-palladium-(0), bis-tri-cyclohexylphosphine-palladium-(0), [1,2-bis(diphenylphosphino)ethane]palladium-II-dichloride or [1,3-bis(diphenylphosphino)propane]palladium-II-dichloride, but preferably [1,1′-bis(diphenylphosphino)ferrocene]-palladium-II-dichloride-dichloromethane complex, as well as a base such as for example sodium carbonate, potassium carbonate, caesium carbonate, triethylamine or N,N-diisopropyl-N-ethyl-amine, but preferably potassium carbonate, in a solvent such as tetrahydrofuran, 1,4-dioxane, acetonitrile or N,N-dimethylformamide, optionally with the addition of water, at temperatures between 30° C. and 150° C., but preferably between 50° C. and 120° C., to obtain the compounds of general formula IX.

Sources & evidence

ORD record
ord-9cb61d4cf61d47778b1978389b5a2591
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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