Dimethyl Carbonate → HCID 131728965, compound

HRID 2428166Notes

Reaction equation

[H-].[Na+].[C:3](=O)([O:6]C)[O:4][CH3:5].[C:9]([O:13][C:14]([N:16]1[CH:21]2[CH2:22][CH2:23][CH:17]1[CH2:18][C:19](=[O:24])[CH2:20]2)=[O:15])([CH3:12])([CH3:11])[CH3:10].[NH4+].[Cl-]>C1CCCCC1.CO>[CH3:5][O:4][C:3]([C:20]1[C@@H:21]2[N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:15])[C@H:17]([CH2:18][C:19]=1[OH:24])[CH2:23][CH2:22]2)=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

temperatureThe mixture was heated
temperatureto reflux
temperatureThe mixture was heated
temperatureto reflux for 3 h
customseparated
extractionlayer was extracted with CH2Cl2 several times
washextracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (EtOAc/heptane 3:7)

Sources & evidence

ORD record: ord-f1d28c47e0e44a46a59f668e30e74bc4
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968720B2

Reaction notes

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