4-Methylquinoline → HCID 44239660, compound

Temperature

25 °C

H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 1-2 min to a stirred solution of lepidine 1a (132 μL, 1.0 mmol), concentrated H2SO4 (107 μL, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at room temperature. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at room temperature for 30 min. Further H2O2(0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred for 15 min, then poured into a 0.2 M solution of NaOH (30 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with Et2O (2 x 25 mL). The combined organic extracts were washed with brine (1 x 30 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography using EtOAc / hexanes (3:7) as eluent to give a mixture of lepidine 1a and desired product 2a (25 mg), and the desired product 2a (82 mg, 40%) as a solid. An analytical portion of the product 2a was recrystallized from EtOAc / hexanes for data purposes

ORD record

ord-89c7d517418648fd92734995b148b41b

Source dataset

Minisci dataset from Roche

DOI

10.1021/jo9010624