Trimethylsilyldiazomethane → Methyl 2-amino-5,6,7,8-tetrahydronaphthalene-1-carboxylate

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Reaction Steps

The white solid from Example 128B (7.17 g, 24.61 mmol) was dissolved in benzene (250 ml) and methanol (62 ml). To the stirring solution was added 2 M trimethylsilyldiazomethane (12.3 ml) until the yellow color persisted for ten minutes. The reaction was then stirred at room temperature or 1 hour. To the solution was added acetic acid until the yellow color disappeared. The solvent was then removed. The crude material (7.52 g, 24.61 mmol) was dissolved in acetic acid (100 mL) and Pt2O (3.50 g, 15.4 mmol) was added shaken in a reactor pressurized with 60 psi of H2 at 25° C. for 80 hours, filtered, and concentrated. The concentrate was treated with dichloromethane (70 mL) and TFA (12 mL) and stirred for 3 hours. The organic layer was washed with NaOH (2×250 mL) and brine (200 mL), dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 206+H)+; 1H NMR (300 MHz, DMSO-d6) δ 6.83 (d, 1H), 6.53 (d, 1H), 5.26 (bs, 2H), 3.78 (s, 3H), 2.62 (m, 2H), 2.57 (m, 2H), 1.64 (m, 4H).

Provenance & Evidence