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6: IR(neat) 2216, 2246 cm-1. 1H NMR (200 MHz, CDCl3): δ 1.35-1.90 (11 H, m), 2.00 (1 H, dm, J = 10.6 Hz), 2.15 (2 H, t, J = 6.5 Hz), 2.95 (1 H, dm, J = 12.0 Hz), 3.12 (1 H, tm, J = 12.0 Hz), 7.15-7.35 (5 H, m).
[13]
C NMR (50 MHz, CDCl3): δ 17.34, 22.25, 23.16, 25.69, 26.20, 36.03, 38.13, 53.35, 61.52, 119.81, 120.64,
127.03, 127.52, 129.58, 149.35. C17H21N3: calcd 267.1736, found 267.1737 (MS). C17H21N3: calcd. C 76.37, H 7.92, N 15.72; found C 76.11, H 8.02, N 15.56.
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A solution (20 mL, THF) of 6 (0.5 g, 1.87 mmol) was cooled to -30 °C and treated dropwise (by syringe) with a
2 M solution of LDA (0.94 mL, 1.87 mmol). The solution was allowed to warm to -20
°C and maintained at that temperature for 1 h, before being stirred at r.t. for 3
h. The reaction mixture was quenched with water and extracted with CH2Cl2. The organic phases were combined, dried over MgSO4, and concentrated in vacuo. The crude material was purified over a silica column
(diethyl ether-petroleum ether, 1:1) to afford 8 (0.433 g, 87%).
