Triethylamine → (2s)-Methyl 2-((6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methylamino)-4-methylpentanoate

Participants

Reaction Steps

Synthesized according to the general procedure as described in Example 1a using L-leucine methyl ester hydrochloride (2.0 gm, 11.0 mmol), THF (25 mL), MgSO4 (2.24 gm, 18.7 mmol), (1R)-(−) myrtenal (3.30 g, 22.0 mmol), Et3N (1.54 mL, 11.0 mmol), sodium borohydride (832 mg, 22.0 mmol), and methanol (20 mL) to give 11l (1.56 gm, 51%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.82 (3H, s), 0.89 (3H, d, J=6.59 Hz), 0.91 (3H d, J=6.83 Hz), 1.15 (1H, d, J=8.54 Hz), 1.27 (3H, s), 1.38-1.54 (3H, m), 1.68 (1H, m), 2.08 (2H, d, J=5.37 Hz), 2.24 (2H, q, J=16.11 Hz), 2.32-2.4 (1H, m), 2.94 (1H, dd, J=1.7, 13.91 Hz), 3.08 (1H, dd, J=1.46, 13.67 Hz), 3.29 (1H, t, J=7.32 Hz), 3.71 (3H, s), 5.36 (1H, s). ESI-MS: 302.2 (M+23).

Provenance & Evidence