ChemicalBook CAS DataBase List tert-Butyl 4-methylenepiperidine-1-carboxylate

tert-Butyl 4-methylenepiperidine-1-carboxylate synthesis

8synthesis methods

Product Name:tert-Butyl 4-methylenepiperidine-1-carboxylate
CAS Number:159635-49-1
Molecular formula:C11H19NO2
Molecular Weight:197.27

79099-07-3 Synthesis

79099-07-3
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tert-Butyl 4-methylenepiperidine-1-carboxylate

159635-49-1
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Yield:159635-49-1 99%

Reaction Conditions:

Stage #1: Methyltriphenylphosphonium bromidewith n-butyllithium in tetrahydrofuran at -78; for 1 h;
Stage #2: N-tert-butyloxycarbonylpiperidin-4-one in tetrahydrofuran at -78 - 20;

Steps:

65

[0242] To a solution of methyl triphenylphosphonium bromide (5.4g, 15.05mmol) in THF (lOOmL) was added slowly butyl lithium (2M, 15.05mmol) at -78°C. The mixture was allowed to stir for one hour and N-Boc-piperidinone (2g, 10.03mmol) was added. The mixture was warmed to room temperature and stirred overnight. The THF was evaporatedand the residue was partitioned between between water and ethyl acetate. The organic layer was washed with brine and dried over sodium sulphate, filtered and concentrated. The compound was purified by column chromatography (30% Hexanes/EtOAc) to provide the title compound (1.96g, 99%).

References:

WO2006/20879,2006,A1 Location in patent:Page/Page column 101-102