Reaction SMILES: C([O-])(=O)C.[NH4+].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13](=O)[CH2:12][CH2:11]2.C([BH3-])#[N:27].[Na+]>CO>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C@@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@@H:13]([NH2:27])[CH2:12][CH2:11]2
Reactant: [BH3-]C#N
Reactant: COc1ccc2c(c1)CCC(=O)C2Cc1ccccc1
Agent: CC(=O)[O-]
Agent: [NH4+]
Agent: [Na+]
Solvent: CO
Product: COc1ccc2c(c1)CC[C@H](N)[C@@H]2Cc1ccccc1
Temperature: 25 °C

Procedure:
Compound 5 (0.464 g, 1.8 mmol) was placed in a 250 mL Parr shaker bottle and dissolved in ethyl acetate (25 mL). Separately, 10% palladium on carbon (0.029 g) was placed in a vial and to it was added methanol (25 mL) in order to create a slurry. This material was then carefully added to the Parr vessel and the mixture was hydrogenated under a pressure of approximately 50 psi for 19 hours. The reaction solution was filtered over a pad of Celite. The solvents were removed in vacuo and the resulting oil was purified by column chromatography (silica gel column (dimensions 2.5×26 cm); 25% ethyl acetate:75% hexanes (v/v) as the eluent). After evaporation of the appropriate fractions, 3,4-dihydro-6-methoxy-1-(phenylmethyl)-2(1H)-naphthalenone 4 was obtained as an off-white oil (0.40 g, 1.50 mmol) (FIG. 2). ##STR10## D. Ammonium acetate (10.7 g, 138 mmol) was added to a solution of 3,4-dihydro-6-methoxy-1-(phenylmethyl)-2(1H)-naphthalenone 4 (3.64 g, 13.6 mmol) in methanol (530 mL) in a I L round-bottom flask with vigorous stirring. Sodium cyanoborohydride (4.29 g, 68.3 mmol) was added and the flask was flushed with argon. A condenser was attached, and the solution was heated at reflux for 21 hours. The solution was cooled to room temperature and the solvents were removed in vacuo. The cream colored solid was dissolved in a mixture of ethyl ether (600 mL) and 0.1 M sodium hydroxide solution (225 mL). The aqueous phase was removed and the organics were washed with an additional 0.1 M sodium hydroxide solution (1×225 mL), and then with water (1×200 mL). The combined aqueous extracts were back extracted with ethyl ether (3×100 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and the solvents were removed in vacuo to afford cis-1,2,3,4-tetrahydro-6-methoxy-1-(phenylmethyl)-2-naphthalenamine 6. The crude product was dissolved in ethyl ether (75 mL) and an excess of 1 M hydrogen chloride in ethyl ether was added. This resulted in a precipitate of the product as a HCl salt. The ethyl ether was removed in vacuo and any large chunks were crushed with a spatula. Ethyl acetate (25 mL) was added, the resultant slurry was heated to reflux and then cooled to room temperature. The solids were filtered off and rinsed with a small portion of ethyl acetate and then with ethyl ether and dried via aspiration to afford cis-1,2,3,4-tetrahydro-6-methoxy-1-(phenylmethyl)-2-naphthalenamine hydrochloride 6a as an off-white powder (2.13 g, 7.0 mmol). MS (MH+) 268; 1H NMR (CDCl3) δ2.05-2.30 (m, 2H), 2.50-2.60 (m, 1H), 2.83-3.03 (m, 3H), 3.30-3.40 (m, 2H), 3.71 (s, 3H), 6.00 (d, 1H), 6.35 (dd, 1H), 6.60 (d, 1H), 7.02-7.16 (m, 5H), 8.53 (bs, 1H), 8.96 (bs, 2H) (FIG. 3). ##STR11##