HCID 12036867, compound → HCID 67020382, compound

Participants

Reaction Steps

2-Propionyl-(6-methyl-6-azabicylo[3.2.2]non-2-ene) [22] A flask was charged with LiAlH4 (410 mg, 10.8 mmol) and dry THF (20 mL), giving a slurry. A solution of 21 (645 mg, 2.15 mmol) in dry THF (30 mL) was added dropwise with stirring, and the reaction was then heated to reflux for 1 h. The reaction was cooled to room temperature, and quenched with dropwise addition of 50 mL EtOAc. The reaction was diluted with H2O (40 mL) and NaCl (sat, aq, 40 mL), and the layers separated. The aqueous layer was extracted with 2×40 mL EtOAc. The organic layers were combined and extracted with 3×50 mL 10% HCl. The aqueous layers were then combined and neutralized with NaHCO3(s) and basified to pH=12 with NaOH (aq). The aqueous layer was extracted with 3×50 mL CH2Cl2, and the organic layers combined, dried (MgSO4), and evaporated to give 2-(1-hydroxy-1-propyl)-(6-methyl-6-azabicyclo[3.2.2]non-2-ene) as a yellow oil (1:1 ratio of diastereomers). Crude yield: 419 mg, 2.17 mmol, 100%).

Provenance & Evidence