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

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

12synthesis methods

Product Name:N-Boc-Piperidine-4-carboxylic acid methyl ester
CAS Number:124443-68-1
Molecular formula:C12H21NO4
Molecular Weight:243.3

67-56-1

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

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

24424-99-5 Synthesis

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

124443-68-1
253 suppliers
$6.00/5g

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

67-56-1 Synthesis

67-56-1
790 suppliers
$9.00/25ml

84358-13-4 Synthesis

84358-13-4
382 suppliers
$5.00/5g

124443-68-1
253 suppliers
$6.00/5g

References

67-56-1 Synthesis

67-56-1
790 suppliers
$9.00/25ml

498-94-2 Synthesis