(2R)-1-phenylpropan-2-amine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared by reacting L-amphetamine (0.49 g, 3.6 mmol) with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.9 g, 3.0 mmol) in dioxan (25 ml) in the presence of diisopropylethylamine (0.58 g, 4.5 mmol) followed by deprotection of the purified product using methanolic ammonia. Evaporation of the reaction mixture provided a gummy residue which crystallized on addition of dichloromethane (10 ml), to provide the title compound (0.26 g, 38%) as a solid, m.p. 132.5°-135.5° C. A further sample of the title compound (0.26 g) was obtained by flash chromatography of the mother liquors. 1H NMR (DMSO-d6)δ 1.22 (3H, d, -- CH3), 2.67-2.79 & 2.92-3.03 (2H, 2m, -- CH2 --), 3.51-3.58 (1H, m, H-5'a), 3.62-3.68 (1H, m, H-5'b), 3.94 (1H, q, H-4'), 4.12 (1H, m, H-3'), 4.41-4.54 (2H, m, H-2' and CH3C H--), 5.06 (1H, t, 5'-OH), 5.22, 5.49 (2H, 2d, 2' and 3'-OH), 5.82 (1H, d, H-1'), 7.10-7.33 (5H, m, Ar--H), 8.28-8.44 (2H, m, H-8 and N--H). The title compound was prepared Evaporation of the reaction mixture provided a gummy residue which crystallized on addition of dichloromethane (10 ml)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-amino-2-(trifluoromethyl)nicotinic acid (15 g, 61.83 mmol) was suspended in a mixture of anhydrous DMF (300 mL) and anhydrous dichloromethane (500 mL). To this was added triethylamine (30.4 mL, 216 mmol), followed by L-amphetamine hydrochloride (12.7 g, 74.2 mmol). HBTU (30.5 g, 80.4 mmol) was added and the mixture was allowed to stir at room temperature overnight. The reaction mixture was concentrated in vacuo to remove dichloromethane. The resultant DMF solution was poured into water, extracted with ethyl acetate (1 L). The organic layer was washed successively with 1N NaOH, saturated sodium bicarbonate, water, dried over sodium sulfate, filtered and concentrated in vacuo to give an oil. This oil was purified by silica gel column chromatography using 40-70% ethyl acetate/heptanes as eluant to provide the product as a colorless foam (18.3 g, 92% yield). 1H NMR (400 MHz, CDCl3) δ 8.2 (d, 1H), 7.2-7.4 (m, 5H), 6.6 (d, 1H), 5.8 (d, 1H), 4.7 (bs, 2H), 4.5 (m, 1H), 2.9 (m, 2H), 1.25 (d, 3H). MS m/z 324.3 (M+H)+. The reaction mixture was concentrated in vacuo to remove dichloromethane The resultant DMF solution was poured into water extracted with ethyl acetate (1 L) The organic layer was washed successively with 1N NaOH, saturated sodium bicarbonate, water dried over sodium sulfate filtered concentrated in vacuo to give an oil This oil was purified by silica gel column chromatography