Dichloromethane → HCID 66700208, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl (2R,5R)-2-(3-{[(2-fluorophenyl)methyl]oxy}phenyl)-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (D46, 200 mg, 0.45 mmol) in dichloromethane (2 mL) cooled at 0° C., was added TFA (0.4 mL) dropwise and the ice-bath removed. After 1 h the solvent was evaporated under vacuum and the crude mixture purified by SCX column to give the title compound as the free base (154 mg, quant.); Rt (HPLC) 3.58 min. The free base (77 mg, 0.23 mmol) was dissolved in dichloromethane (2.5 mL), and o the resulting solution cooled at 0° C. HCl (0.29 mL of a 1M solution in diethyl ether, 0.29 mmol) was added dropwise. After 15 min the solvent was removed under reduced pressure and the resulting solid triturated with diethyl ether to give the title compound (68 mg, 80%); Rt (HPLC) 3.72 min. MS: (ES/+) m/z: 341 [MH+]; C20H21FN2O2 requires 340; 1H NMR (500 MHz, DMSO-d6) δ (ppm): 10.13 (br. s., 1H), 8.94 (br. s., 1H), 8.39-8.53 (m, 1H); 7.57 (t, 1H), 7.41-7.47 (m, 1H); 7.38 (t, 1H), 7.31-7.35 (m, 1H); 7.22-7.30 (m, 2H); 7.17 (d, 1H), 7.10 (d, 1H), 5.13-5.18 (m, 2H); 4.72 (br. s, 1H), 3.34-3.41 (m, 2H); 2.25-2.68 (m, 5H), 2.12 (br. s, 1H).

Provenance & Evidence