Triethylamine → HCID 86648188, compound

Participants

Reaction Steps

(S)-2-amino-1-((3aS,4S,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)ethanol (2-6) (3.22 g, 15.0 mmol, 1.0 eq) was dissolved in dioxane (150 mL). 2,3-Dichloropyrazine (4.46 g, 29.9 mmol, 2 equiv) was added followed by triethylamine (8.34 mL, 59.8 mmol, 4 equiv) and the reaction mixture was heated to reflux overnight. Concentration and purification via flash chromatography on a silica gel column (ethyl acetate/hexanes) yielded desired (S)-2-(3-chloropyrazin-2-ylamino)-1-((3aS,4S,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)ethanol (2-7) as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 7.88 (dd, J=5.5, 2.7 Hz, 1H); 7.60 (d, J=2.7 Hz, 1H); 5.74 (d, J=31.9 Hz, 1H); 4.68-4.63 (m, 1H); 4.34 (t, J=5.4 Hz, 1H); 3.88 (ddd, J=14.5, 6.7, 2.5 Hz, 1H); 3.81-3.69 (m, 2H); 3.63-3.46 (m, 2H); 2.15-2.04 (m, 1H); 2.03-1.88 (m, 1H); 1.83-1.72 (m, 1H); 1.69-1.52 (m, 1H); 1.50 (d, J=13.2 Hz, 3H); 1.32 (d, J=4.5 Hz, 3H). LRMS m/z (M+H) 313.9 found, 314.1 required.

Provenance & Evidence