Triethylamine → HCID 86648185, compound

Participants

Reaction Conditions

Reaction Steps

(S)-2-amino-1-((3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)ethanol (1-5) (2 g, 3.82 mmol, 1.0 eq) was dissolved in DMF (15.3 mL). 2,3-Dichloropyrazine (1.20 g, 7.63 mmol, 2 equiv) was added followed by triethylamine (2.13 mL, 15.3 mmol, 4 equiv). The reaction was stirred 20 hours at 60° C. Over a period of 52 hours 2,3-dichloropyrazine (299 mg, 1.91 mmol, 0.5 equiv) was added every 3 hours. The reaction was concentrated and purified via flash chromatography on silica gel column (ethyl acetate/hexanes) to yield (S)-2-(3-chloropyrazin-2-ylamino)-1-((3aS,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)ethanol (1-6) as a white foam. 1H NMR (500 MHz, CDCl3) δ 7.91 (d, 1H, J=1.5 Hz), 7.62 (d, 1H, J=1.5 Hz), 7.21-7.48 (m, 15H), 5.84 (2 s, 1H), 5.62 (m, 1H), 4.97 (t, 1H, J=6 Hz), 4.60-4.77 (2 d, 1H, J=7 Hz), 3.95 (d, 1H, J=14 Hz), 3.75 (m, 2H), 3.31 (m, 1H), 2.57-2.88 (m, 2H), 1.36 (s, 3H), 1.32 (s, 3H).

Provenance & Evidence