Pentane → HCID 67467267, compound

HRID 2202786Notes

Reaction equation

HRID 2202786 reaction equation
C([Li])(C)(C)C.CCCCC.I[C:12]1[C:17]([CH3:18])=[N:16][CH:15]=[CH:14][N:13]=1.[C:19]([O:23][C:24]([N:26]1[CH:31]2[CH2:32][CH2:33][CH:27]1[CH2:28][C:29](=[O:34])[CH2:30]2)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C(OCC)C.C(OCC)(=O)C.O>[C:19]([O:23][C:24]([N:26]1[CH:31]2[CH2:32][CH2:33][CH:27]1[CH2:28][C:29]([OH:34])([C:12]1[C:17]([CH3:18])=[N:16][CH:15]=[CH:14][N:13]=1)[CH2:30]2)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

8

Reactant 4

HCID 8003PentaneHCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 108786642-IODO-3-METHYLPYRAZINEHCID 178418306HCID 178418306, compound

Product 1

HCID 67467267HCID 67467267, compoundYield 35.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

t-Butyl lithium in pentane (1.7 M, 3.8 mL, 6.46 mmol) was added dropwise to a solution of 2-iodo-3-methylpyrazine (0.7 g, 3.18 mmol) in diethyl ether (20 mL) at −50° C. under nitrogen and stirred for 30 minutes. A solution of 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.19 g, 0.88 mmol) in diethyl ether (10 mL) was added dropwise and stirred at −50° C. for 1 hour. The reaction mixture was warmed to room temperature, water and ethyl acetate were added, the organics separated, dried over sodium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with ethyl acetate/cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.1 g) as a pale yellow oil. LCMS m/z 320.2 [M+H]+. R.T.=3.55 min (Analytical Method 3).

Workup

  1. stirringstirred at −50° C. for 1 hour
  2. dry with materialthe organics separated, dried over sodium sulphate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation under vacuum
  5. customThe residue was purified by flash chromatography on silica eluting with ethyl acetate/cyclohexane
  6. additionThe fractions containing the desired product
  7. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-6e01b710e7354d8a901faf7eee118e87
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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