ChemicalBook CAS DataBase List 4-Bromomethypiperidine-1-carboxylic acid tert-butyl ester

4-Bromomethypiperidine-1-carboxylic acid tert-butyl ester synthesis

5synthesis methods

Product Name:4-Bromomethypiperidine-1-carboxylic acid tert-butyl ester
CAS Number:158407-04-6
Molecular formula:C11H20BrNO2
Molecular Weight:278.19

4-Bromomethypiperidine-1-carboxylic acid tert-butyl ester. 4-N-Boc-piperidine-methanol (200 mg, 0.93 mmol) was dissolved in diethyl ether (9 mL) and carbon tetrabromide (370 mg, 1.1 mmol) and PPh3 (292 mg, 1.1 mmol) were added at rt. The reaction was allowed to stir for 18 h at rt and filtered over a pad of celite. The filtrate was concentrated and purified by flash chromatography (hexane/EtOAc, 1:0 → 4:1) to give the title compound. Yield 55 mg. 1 (400 MHz, DMSO-d6) δ ppm 4.02-3.98 (m, 2 H), 3.47 (d, 2 H), 2.78-2.65 (m, 2 H), 1.89-1.74 (m, 3 H), 1.45 (s, 9 H), 1.12-0.98 (m, 2 H).

123855-51-6 Synthesis

123855-51-6
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4-Bromomethypiperidine-1-carboxylic acid tert-butyl ester

158407-04-6
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$5.00/100mg

Yield:158407-04-6 94%

Reaction Conditions:

with carbon tetrabromide;triphenylphosphine in dichloromethane at 0 - 20; for 22 h;

Steps:

14
Compound 14; EPO N-BOC piperidine-4-methanol (1 g; 46.5 mmol) and carbon tetrabromide (1.7 g; 51.3 mmol) were dissolved in dichloromethane (20 ml) and cooled to 0 ⁰C. Triphenyl phosphine (0.98 g; 37.3 mmol) was added and the reaction stirred at room temperature for 16 hours. Further triphenyl phosphine (0.4 g; 15.7 mmol) and carbon tetrabromide (0.24 g; 7.2 mmol) were added and stirring continued for 6 hours. The solvent was evaporated and the residue chromatograplied on silica. N-BOC piperidine-4 methyl bromide was eluted with 20% ethyl acetate in heptane (1.22 g, 94%).

References:

CURIS, INC. WO2006/50506, 2006, A1 Location in patent:Page/Page column 120-121

FullText

161975-39-9 Synthesis