Pyridine → HCID 67285850, compound

Participants

Reaction Conditions

Reaction Steps

(3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (1-1) (1.44 g, 3.36 mmol, 1.0 equiv) as dissolved in DCM (11.2 mL). Pyridine (0.489 mL, 6.05 mmol, 1.8 equiv) was added and the mixture stirred at 0° C. After 1 hour DMAP (164 mg, 1.34 mmol, 0.4 equiv) was added followed by methyl chloroformate (1.04 mL, 13.44 mmol, 4 equiv). The resulting mixture was stirred 12 h, and the temperature was allowed to slowly increase to 23° C. The reaction was partitioned between DCM and water, and the organic layer was separated and washed with water, dried (MgSO4), and concentrated to yield (3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methyl carbonate (1-2) as a white foam. 1H NMR (00 MHz, CDCl3) δ 7.21-7.47 (m, 15H), 6.03 (d, 1H, J=3.0 Hz), 5.32 (brm, 1H), 4.93 (t, 1H, J=9 Hz), 4.85 (d, 1H, J=10 Hz), 3.96 (d, 1H, J=24.5 Hz), 3.83 (s, 3H), 3.67 (d, 1H, J=24.5 Hz), 1.36 (s, 3H), 1.34 (s, 3H).

Provenance & Evidence