Electric Literature of 1014645-87-4,Some common heterocyclic compound, 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, molecular formula is C11H14ClNO2, 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.
General procedure: To a solution of selected acid (1 eq) in DMF, HCTU (1.1 eq) and DIPEA (2.5 eq) were added in sequence and the resulting mixture was stirred 30 min before adding the selected amine (1.1 eq). The mixture was left stirring at RT for 1-18 hrs then the reaction mixture was partitioned between EtOAc and H2O and the organic phase was separated. The aqueous phase was washed with EtOAc. All the collected organic phases were washed with NaCl sat. sol., dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was purified on SPE-Si cartridge or Biotage SNAP-Si column eluting with a mixture of DCM/EtOAc from 100:0 to 95:5 affording the title amide compound. The title compound (D58) (250 mg) was prepared according to the general procedure for amides preparation (Method C) starting from 1-(tert-butoxycarbonyl)-4,4-dimethylpiperidine-2-carboxylic acid (320 mg; described in J. Med. Chem. 1997, 40, 2491-2501) and methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (312 mg). Reaction time: 18 hrsMS: (ES/+) m/z: 431.4 [MH+] C24H34N2O5 requires 430.251H NMR (400 MHz, CHCl3-d) delta (ppm): 7.96 (d, J=8.2 Hz, 2H), 7.32-7.29 (m, 2H), 6.82-6.59 (m, 1H), 4.65 (d, J=4.4 Hz, 1H), 4.02 (br. s., 1H), 3.92 (s, 3H), 3.00 (d, J=10.6 Hz, 1H), 2.18 (d, J=12.9 Hz, 1H), 1.50 (s, 9H), 1.43-1.29 (m, 7H), 0.96 (s, 3H), 0.84 (s, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, its application will become more common.
Reference:
Patent; Borriello, Manuela; Pucci, Sabrina; Stasi, Luigi Piero; Rovati, Lucio; US2015/87626; (2015); A1;,
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