1,1-Dimethylhydrazine → HCID 16222232, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-2-tert-butyl 1-methyl 6-(2-chloro-5-nitrobenzyloxy)-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate prepared following procedure 2 (56 mg, 0.12 mmol) in MeOH (5 mL) was added FeCl3.6H2O (10 mg, 0.04 mmol) followed by the addition of 1,1-dimethylhydrazine (0.5 g, 7 mmol). The reaction was refluxed at 85° C. for 16 h and filtered. The filtrate was concentrated and purified by preparative HPLC (Phenomenex 20×100 mm eluting with 0-100% MeOH/H2O (90% in H2O, 0.1% TFA) gradient over 8 min with flow rate 25 mL/min) to yield (R)-2-tert-butyl 1-methyl 6-(5-amino-2-chlorobenzyloxy)-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate as a yellow oil (17 mg, 32%). HPLC retention time (Method C)=3.35 min. LC/MS (ESI) (M+Na)+=469. 1H NMR (400 MHz, CDCl3) δ ppm 1.46 (s, 5H), 1.48 (s, 4H), 2.69-3.00 (m, 2H), 3.57-3.85 (m, 5H), 5.04 (s, 2H), 5.36 (s, 0.5H), 5.52 (s, 0.5H), 6.71 (s, 1H), 6.80 (m, 1H), 6.98 (d, J=7.47 Hz, 1H), 7.27-7.40 (m, 3H).

Provenance & Evidence