Butyl bromide → HCID 58465799, compound

HRID 1842453Notes

Reaction equation

HRID 1842453 reaction equation
FC(F)(F)C(O)=O.[CH2:8]1[NH:13][CH2:12][CH2:11][N:10]2[CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=[C:9]12.Br[CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:23]([N:13]1[CH2:12][CH2:11][N:10]2[CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=[C:9]2[CH2:8]1)[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 67437166HCID 67437166, compound

Product 1

HCID 58465799HCID 58465799, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate trifluoroacetate (2.6 g, 13.4 mmol) and 1-bromobutane (3.67 g, 26.8 mmol) in acetonitrile (26 mL) was added potassium carbonate (2.45 g, 17.7 mmol). The resulting mixture was refluxed overnight. The solvent was then evaporated to give a solid residue. Purification via flash chromatography (petroleum ether:EtOAc, 10:1) afforded ethyl 2-butyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate Intermediate 11 (0.7 g, 21%). 1H NMR (CDCl3, 300 MHz) δ7.11 (s, 1 H), 6.18 (s, 1 H), 4.25 (m, 2 H), 3.99 (m, 2 H), 3.53 (s, 2 H), 2.82 (t, J=5.6 Hz, 2 H), 2.46 (t, J=7.4 Hz, 2 H), 1.46 (m, 2 H), 1.30 (m, 2 H), 1.25 (t, J=7.1 Hz, 3 H), 0.87 (t, J=7.3 Hz, 2 H).

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. customThe solvent was then evaporated
  3. customto give a solid residue
  4. customPurification via flash chromatography (petroleum ether:EtOAc, 10:1)

Sources & evidence

ORD record
ord-579c44b198e5442da578a60d3f3d1132
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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