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ChemicalBook CAS DataBase List N-Boc-Piperidine-4-carboxylic acid methyl ester
124443-68-1

N-Boc-Piperidine-4-carboxylic acid methyl ester synthesis

12synthesis methods
Methanol

67-56-1

N-BOC-piperidine-4-carboxylic acid

84358-13-4

N-Boc-Piperidine-4-carboxylic acid methyl ester

124443-68-1

General procedure for the synthesis of methyl 1-tert-butoxycarbonyl-4-piperidinecarboxylate from methanol and 1-Boc-4-piperidinecarboxylic acid: a hexane solution of trimethylmethylsilyl diazomethane (2.00 M, 52.9 mL, 106 mmol) was added slowly and dropwise at 0 °C to a 1-tert-butoxycarbonyl-piperidine-4-carboxylic acid (12.14 g, 52.95 mmol) acetonitrile ( 100 mL) suspension. Methanol (10 mL) was then added. The reaction mixture was allowed to stand at 0 °C for 30 min and then stirred at room temperature for 3 h. The reaction was carried out under reduced pressure. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography [hexane/ethyl acetate (4.5:1, v/v)] to afford 1-tert-butyl 4-methylpiperidine-1,4-dicarboxylate as a colorless oil (11.5 g, 90% yield). The structure of the product was confirmed by 1H NMR (400 MHz, d6-DMSO): δ 4.02 (dt, 2H, J = 3.5, 13.7 Hz), 3.69 (s, 3H), 2.82 (ddd, 2H, J = 3, 11.5, 14.5 Hz), 2.45 (tt, 1H, J = 3.9, 11.5 Hz), 1.90-1.84 ( m, 2H), 1.67-1.57 (m, 2H), 1.45 (s, 9H). Mass spectral analysis (ES) showed m/z 265.8 (MNa+); calculated value: 243.1 (M).

2971-79-1 Synthesis
Methyl isonipecotate

2971-79-1
273 suppliers
$10.00/10g

24424-99-5 Synthesis
Di-tert-butyl dicarbonate

24424-99-5
867 suppliers
$13.50/25G

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Yield:124443-68-1 98%

Reaction Conditions:

with triethylamine in dichloromethane at 25; for 12 h;Product distribution / selectivity;

Steps:

A.2.1

Synthesis of 9-(Azetidin-1-yl)-9-phenyl-3-azaspiro[5.5]undecane Trifluoroacetate (A4); Step-1: 1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate; To a stirred solution of methyl isonipecotate (127.2 mmol, 1 eq) in dichloromethane (200 ml) were added di-tert-butyldicarbonate (190.8 mmol, 1.5 eq) and triethylamine (254.4 mmol, 2.0 eq). The reaction mixture was stirred for 12 h at 25° C. It was then diluted with dichloromethane (100 ml) and washed with water (50 ml) and brine (50 ml). The organic layer was separated, dried over Na2SO4, concentrated and employed in the next step without further purification. Yield: 98%

References:

US2010/113417,2010,A1 Location in patent:Page/Page column 36

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