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(2) Synthesis of Methyl (R)-4-(1-Aminoethyl)benzoate By similar reaction and treatment to that in Example 95(2) using (R)-4-(1-aminoethyl)benzoic acid instead of 4-(1-acetamido-1-methylethyl)benzoic acid, the title compound can be obtained.
methyl (R)-4-(1-(4-(4-Fluorophenyl)piperazin-1-yl)ethyl)benzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
(3) Synthesis of Methyl (R)-4-(1-(4-(4-Fluorophenyl)piperazin-1-yl)ethyl)benzoate By similar reaction and treatment to that in Example 68(13) using <strong>[912342-10-0]methyl (R)-4-(1-aminoethyl)benzoate</strong> instead of N-(4-(1-amino-1-methylethyl)phenylmethyl)acetamide, the title compound can be obtained.
Example 216(R)-methyl 4-(1-((1-methylcyclohexyl)methylamino)ethyl)benzoateTo a solution of <strong>[912342-10-0](R)-methyl 4-(1-aminoethyl)benzoate</strong> (0.12 g, 0.67 mmol) in methanol (2.97 mL, 73.33 mmol) was added 1-methylcyclohexane-1-carboxaldehyde (0.093 g, 0.74 mmol) and acetic acid (0.152 mL, 2.67 mmol). The reaction was stirred for 1 hour at room temperature whereupon sodium cyanoborohydride (63.1 mg, 1.00 mmol) was added and the mixture further stirred at room temperature overnight. The solvent was evaporated and the residual sodium cyanoborohydride quenched with saturated aqueous NaHCO3. The mixture was extracted into ethyl acetate, the organic layer washed with brine and the solvent evaporated to dryness. The residue obtained was purified via silica chromatography (0-5% MeOH/DCM) to afford the title compound as a colorless oil (123.0 mg, 63%). LC-MS: (FA) ES+290.
Example 215(R)-methyl 4-(1-aminoethyl)benzoateTo a solution of (R)-4-(1-amino-ethyl)-benzoic acid hydrochloride (0.20 g, 0.99 mmol) in methanol (3.2 mL) was added sulfuric acid (5.29 muL, 0.0992 mmol). The resulting solution was heated at reflux overnight. The methanol was removed under reduced pressure leaving a light brown oil which was partitioned between half-saturated sodium bicarbonate solution (50 mL) and ethyl acetate (75 mL). The aqueous phase was extracted with additional ethyl acetate (50 mL). The extracts were combined, washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure, Purification via silica chromatography (0-50% EtOAc/hexane) afforded product as a white solid (0.124 g, 70%). LC-MS: (FA) ES+180.
To a stirred solution of commercially available <strong>[912342-10-0](R)-methyl-4-(1-aminoethyl)benzoate</strong> (i.o g, 5.58 mmol) in CHC13 (io mL) was added TFAA (2.35 g, 11.17 mmol) at 10-15 Cdropwise and the resulting reaction mixture was stirred at 25 0C for 40 mm. The progress of the reaction was monitored by UPLC-MS. The reaction mixture was poured into crushed ice-water and extracted with EtOAc. The combined organic layers were washed successively with saturated NaHCO3 solution and brine solution and then dried over anhydrous Na2SO4. The filtered organics were evaporated under reduced pressureto afford the titled compound (1.4 g, yield 91% and purity >98%) as a white solid. LCMS m/z: 274.05 [M+H].
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