18-Crown-6 → HCID 86753720, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (3S,4R,5S,6S)-6-diphenylmethyl-5-hydroxy-1-azabicyclo[2.2.2]octane-3-carboxylic acid hydrochloride (obtained in Example 1 (iii); 110 mg, 0.3 mmol) in DME (3 ml) was added potassium t-butoxide (130 mg, 1.2 mmol) followed by 18-crown-6 (300 mg, 1.2 mmol) at room temperature. To this solution was added 5-isopropyl-2-methoxybenzyl bromide (300 mg, 1.2 mmol) in DME (3 ml) at 0° C. The mixture was stirred at 0° C. for 1 hour and at room temperature for 1 hour, quenched with H2O (10 ml), and extracted with CH2Cl2 three times. The combined extracts were dried over Na2SO4 and concentrated. The crude was purified by a column chromatography on silicagel to give a title compound (120 mg, 0.23 mmol, 78%).

Provenance & Evidence