HCID 69621453, compound → HCID 9838075, compound

Participants

Reaction Steps

Finely ground Cd/Pb couple (3.12 g) was added portion wise to a solution of 105 (1 g, 2.2 mmol) THF (10 mL) and NH4OAc (1M, 10 mL). The reaction was followed by TLC (EtOAc), when no starting material was present, the mixture was poured into ethyl acetate (400 mL). The organic phase was dried over MgSO4 and evaporated to yield the crude product, which was purified by flash chromatography (EtOAc) to give of the pure compound as a pale yellow oil (0.45 g, 78%): 1H NMR (270 MHz, CDCl3) δ2.08 (m, 2H); 2.29 (m, 2H); 3.53-3.63 (m, 1H); 3.72 (m, 1H); 3.79-3.85 (m, 1H); 3.93 (s, 3H); 3.96 (s, 3H); 6.82 (s, 1H); 7.52 (s, 1H); 7.68 (d, J=4.4, 1H). 13C NMR (67.8 MHz, CDCl3) δ24.2; 29.6; 46.7; 53.7; 56.0; 56.1; 109.4; 111.2; 140.7; 147.5; 151.3; 162.5; 164.6. IR (Nujol): cm−1 3000-2800, 1601, 1450, 1434, 1500, 1453, 1263, 1217, 1010, 908, 735. MS: m/e (relative intensity) 260 (M+, 100), 245 (50), 231 (25), 217 (10), 191 (20), 164 (25), 136 (20), 121 (5), 93 (8), 70 (10). HRMS Calculated for C14H16N2O3: 260.1160. Found: 260.1161. [α]25D=+1004.7° (c=0.17, CHCl3).

Provenance & Evidence