Hydrochloric Acid → HCID 86662215, compound

Participants

Reaction Steps

A flame-dried 1-neck flask was charged with 50 mL of distilled THF and 0.130 g (0.498 mmol) of the cis lactam 15a were added. A 1.0 M solution of BH3 in THF (2.49 mL, 2.49 mmol) was added dropwise to the flask and the reaction was heated at reflux overnight. The reaction was then cooled to room temperature, quenched carefully with H2O, and evaporated to about one-third the volume. Following the addition of 10 mL 2N HCl, the solution was stirred at ambient temperature for 4 h. The aqueous solution was washed once with Et2O, basified with NH4OH, and extracted with CH2Cl2 (3×25 mL). The organic layers were combined, dried over Na2SO4, filtered, and evaporated to yield a colorless residue, which was dissolved in Et2O and acidified with 6N HCl in EtOH. The solid that formed was collected by filtration to yield 0.084 g (0.297 mmol, 59.6%) of the isoquinoline HCl 17a as a white powder; mp 186° C. (dec). 1H NMR: (500 MHz, DMSO): δ 8.80 (bs, 2H, NH2); 6.87 (m, 2H, ArH); 3.75 (s, 3H, ArOCH3); 3.66 (s, 3H, ArOCH3); 3.18-3.15 (dd, 1H, J=4.2, 12.4 Hz, ArCHCH2NH2); 3.12-3.05 (m, 2H, CH2NH2CH2); 2.99-2.82 (m, 3H, ArCHCH2NH2CH2, ArCH2); 2.59-2.48 (m, 1H, ArCH2); 2.10-1.89 (m, 3H, ArCH2CH2CHCH2); 1.76-1.68 (bd, 1H, J=11.8 Hz, NH2CH2CH2); 1.62-1.54 (m, 1H, ArCH2CH2). ESIMS (M+H)=248.

Provenance & Evidence