ChemicalBook CAS DataBase List 4-[(5-bromo-2-pyridinyl)methyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester

4-[(5-bromo-2-pyridinyl)methyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester synthesis

1synthesis methods

Product Name:4-[(5-bromo-2-pyridinyl)methyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester
CAS Number:253594-54-6
Molecular formula:C16H23BrN2O2
Molecular Weight:355.27

624-28-2 Synthesis

624-28-2
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159635-49-1 Synthesis

tert-Butyl 4-methylenepiperidine-1-carboxylate

159635-49-1
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4-[(5-bromo-2-pyridinyl)methyl]-1-piperidinecarboxylic
acid 1,1-dimethylethyl ester

253594-54-6
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Yield:253594-54-6 96%

Reaction Conditions:

Stage #1: tert-butyl 4-methylidenepiperidine-1-carboxylatewith 9-borabicyclo[3.3.1]nonane dimer in tetrahydrofuran; for 1 h;Heating;
Stage #2: 2,5-dibromopyridinewith potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ in tetrahydrofuran;water;N,N-dimethyl-formamide at 60; for 3 h;Suzuki coupling;

References:

Vice;Bara;Bauer;Evans;Ford;Josien;McCombie;Miller;Nazareno;Palani;Tagat [Journal of Organic Chemistry,2001,vol. 66,# 7,p. 2487 - 2492]