Triethylamine → HCID 178480557, compound

Participants

Reaction Steps

To a solution of (3S,4S)-4-(4-((E)-(3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)methyl)-2-nitrophenylamino)-1-methylpyrrolidin-3-ol (3.10 mmol, 1.43 g) in isopropanol (85 mL) and triethylamine (9.3 mmol, 1.30 mL) add 5% Pt/C (420 mg) and hydrogenate at 50 psi for 1.5 h. Filter through a plug of diatomaceous earth and wash with isopropanol (50 mL). Add diphenyl cyanocarbonimidate (3.1 mmol, 0.74 g) and stir at room temperature overnight, then heat to reflux for 3 h. Remove the solvent and purify the residue by column chromatography eluting with a gradient from 0% to 20% methanol in methylene chloride to give the title compound as a light brown solid (955 mg, 57%). [α]D23+13.8 (c 0.17, CH3OH); ESI MS m/z 482 [M+H]+.

Provenance & Evidence