1-Methylimidazole → HCID 67466096, compound

HRID 2202780Notes

Reaction equation

C([Li])CCC.[CH3:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[C:12]([O:16][C:17]([N:19]1[CH:24]2[CH2:25][CH2:26][CH:20]1[CH2:21][C:22](=[O:27])[CH2:23]2)=[O:18])([CH3:15])([CH3:14])[CH3:13].[Cl-].[NH4+]>C1COCC1>[C:12]([O:16][C:17]([N:19]1[CH:24]2[CH2:25][CH2:26][CH:20]1[CH2:21][C:22]([OH:27])([C:8]1[N:7]([CH3:6])[CH:11]=[CH:10][N:9]=1)[CH2:23]2)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyl lithium (2.5 M, 1 mL, 2.5 mmol) was added dropwise to a solution of 1-methyl imidazole (0.193 g, 2.35 mmol) in THF (10 mL), under nitrogen at −78° C. 3-Oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.55 g, 2.45 mmol) in THF (2.5 mL) was added and the mixture stirred at −78° C. for 1 hour before warming to room temperature. A solution of saturated aqueous ammonium chloride was added and the mixture extracted into ethyl acetate, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 1:1 ethyl acetate/cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.12 g). LCMS m/z 308.2 [M+H]+. R.T.=2.14 min (Analytical Method 3).

Workup

temperaturebefore warming to room temperature
extractionthe mixture extracted into ethyl acetate
dry with materialdried over magnesium sulphate
filtrationfiltered
customthe solvent removed by evaporation under vacuum
customThe residue was purified by flash chromatography on silica eluting with 1:1 ethyl acetate/cyclohexane
additionThe fractions containing the desired product
concentrationwere concentrated under vacuum

Sources & evidence

ORD record: ord-5eb3189abb5d4162a10c2fe71f615d11
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365564B2

Reaction notes

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