Related Products of 123986-64-1, These common heterocyclic compound, 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
1) Synthesis of 1-[4-[N-(tert-butoxycarbonyl)aminomethyl]benzyl]-4-benzylpiperidine To a solution of 5.0 g (21.07 mM) of 4-[N-(tert-butoxycarbonyl)aminomethyl]-1-phenylmethanol and 5.9 ml (42.33 mM) of triethylamine in THF (42 ml) was added 2.5 ml (32.3 mM) of methanesulfonyl chloride at 0 C. and the mixture was stirred at the prevailing temperature for one hour. The reaction was stopped by adding saturated aqueous solution of sodium hydrogen carbonate and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide 7.21 g (21.07 mM) of crude product as light-brown solid. To a solution of 7.21 g (21.07 mM) of this crude mesylate in ethanol (42 ml) was added 5.9 g (42.33 mM) of triethylamine as well as 3.69 g (21.05 mM) of 4-phenylpiperidine and the mixture was refluxed for 18 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over MgSO4. After concentration, the crude product was purified by column chromatography (ethyl acetate-hexane: 50%) to provide the title compound as light-yellow oil. Yield 5.77 g (69%) 1H-NMR (200 MHz, CDCl3) delta: 1.20-1.40 (2H, m), 1.46 (9H, s), 1.85-2.01 (2H, m), 2.53 (2H, d, J=6.2 Hz), 2.78-2.93 (2H, m), 3.48 (2H, s), 4.29 (2H, d, J=6.0 Hz), 4.70-4.88 (1H, m), 7.07-7.34 (9H, m). IR (neat): 3350, 2924, 1709, 1508, 1452, 1365, 1252, 1173 cm-1.
The synthetic route of 123986-64-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Takeda Chemical Industries, Ltd.; US6235731; (2001); B1;,
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