Category: 123986-64-1

Synthetic Route of 123986-64-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 281,1-Dimethylethyl [(4-{[3-{bis[(5-chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}phenyl)methyl]carbamate; A solution of 5-chloro-N-[(5-chloro-2-thienyl)sulfonyl]-N-[4-(methyloxy)-1 H-indazol-3-yl]-2-thiophenesulfonamide (for a preparation see Intermediate 10)(400 mg, 0.763 mmol), triphenylphosphine (400 mg, 1.52 mmol) and 1,1-dimethylethyl{[4-(hydroxymethyl)phenyl]methyl}carbamate (Maybridge) (362 mg, 1.52 mmol) in THF (3 mL) was added at room temperature DIAD (0.300 mL, 1.52 mmol). The resulting mixture was stirred at 65 C. for 3 hours. The reaction mixture was partitioned between DCM (3 mL) and water (3 mL). The organic phase was separated, and the aqueous layer was further extracted with DCM (3 mL). The combined organic solutions were dried over an hydrophobic frit and evaporated under a nitrogen stream in a blowdown unit. The residue was loaded in dichloromethane on a silica (50 g) cartridge and purified by chromatography on Flashmaster II using a gradient of 0-100% dichloromethane-cyclohexane over 40 min. The appropriate fractions were combined and evaporated in vacuo to give the title compound (498 mg, 88%) as a gum.LCMS (System A) RT=1.48 min, ES+ve m/z 760/762 (M+NH4)+.

The synthetic route of tert-Butyl 4-(hydroxymethyl)benzylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hodgson, Simon Teanby; Lacroix, Yannick Maurice; Procopiou, Pauayiotis Alexandron; US2010/216860; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate, molecular formula is C13H19NO3, 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. Formula: C13H19NO3

3) Synthesis of 1-[4-[N-(tert-butoxycarbonyl)aminomethyl]benzyl]-4-phenylpiperidine 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 then stopped by adding saturated aqueous solution of sodium hydrogen carbonate and the 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 6.72 g (21.07 mM) of crude product as light-brown solid. To a solution of 6.72 g (21.07 mM) of this crude mesylate in ethanol (42 ml) was added 5.9 ml (42.33 mM) of triethylamine as well as 3.40 g (21.09 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 magnesium sulfate. After concentration, the crude product was purified by column chromatography (ethyl acetate-hexane: 50%) to provide the title compound as light-yellow solid. Yield 5.77 g (72%) m.p. 73-74 C. 1H-NMR (200 MHz, CDCl3) delta: 1.46 (9H, s), 1.73-1.88 (4H, m), 1.99-2.19 (1H, m), 2.94-3.08 (2H, m), 3.54 (2H, s), 4.31 (2H, d, J=5.8 Hz), 4.73-4.96 (1H, m), 7.13-7.36 (4H, m). IR (KBr): 3389, 1690, 1518, 1269, 1171 cm-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 123986-64-1, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6235731; (2001); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics