Ammonia → HCID 67285542, compound

Participants

Reaction Conditions

Reaction Steps

(3aS,4S,6aR)-2,2-dimethyl-4-((S)-oxiran-2-yl)-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (1-4) (2 g, 4.0 mmol, 1.0 equiv) was dissolved in a solution of ammonia in methanol (100 mL, 7 N). The mixture was heated in the microwave at 100° C. for 30 min. The reaction was concentrated to afford (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) as an amber solid that was carried to the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.21-7.45 (m, 15H), 5.81 (2 s, 1H), 5.00 (t, 1H, J=5 Hz), 4.57-4.70 (2 d, 1H, J=5.5 Hz), 3.77 (d, 1H, J=14 Hz), 3.66 (d, 1H, J=14 Hz), 3.31 (m, 1H), 2.57-2.88 (m, 2H), 1.30 (s, 3H), 1.29 (s, 3H). LRMS m/z (M+H) 472.1 found, 472.2 required.

Provenance & Evidence