Dimethyl Carbonate → HCID 131728965, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (55-65% mineral oil, 9.82 g, about 225 mmol) in cyclohexane (87.5 mL) was added dimethyl carbonate (21.0 mL, 250 mmol). The mixture was heated to reflux, and a sol. of 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (25.6 g, 113 mmol) in MeOH (0.25 mL) and cyclohexane (62.5 mL) was added over 35 min. The mixture was heated to reflux for 3 h, and was cooled to 0° C. Aq. sat. NH4Cl was added carefully until the phases separated. The org. layer was extracted with CH2Cl2 several times. The combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 3:7) yielded the title compound (29.7 g, 93%). LC-MS: tR=0.96 min.

Provenance & Evidence