反应详情

The title compound was synthesized according to General Method H utilizing cyclopentanecarboxaldehyde (15.0 g, 152.8 mmol, 1.0 eq.), (R)-t-butylsulfinylamide (24.1 g, 198.7 mmol, 1.3 eq.), and flame-dried CuSO4 (73.2 g, 458.5 mmol, 3.0 eq.). The resulting mixture was stirred at rt for 71 h. The reaction mixture was filtered through a pad of Celite and the pad was rinsed with CH2Cl2 (5×100 mL). The combined organic extracts were concentrated under reduced pressure yielding a clear yellow oil (37.2 g). Purification by flash chromatography (SiO2, h=6 cm, Ø=10 cm) using 1:9 EtOAc-cyclohexane as eluent gave the product (23.8 g, 78% isolated yield) as a clear pale yellow oil. 1H NMR (300 MHz, CDCl3) δ ppm 7.99 (d, J=5.5 Hz, 1H), 3.02-2.87 (m, 1H), 1.97-1.78 (m, 2H), 1.78-1.55 (m, 6H), 1.18 (s, 9H).

1. filtrationThe reaction mixture was filtered through a pad of Celite
2. washthe pad was rinsed with CH2Cl2 (5×100 mL)
3. concentrationThe combined organic extracts were concentrated under reduced pressure