Diisopropylamine → HCID 86649625, compound

HRID 1897947Notes

Reaction equation

HRID 1897947 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[N:13]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1.[Br:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38]Br)[N:33]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[Br:31][C:32]1[N:33]=[C:34]([CH2:38][C:16]2([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14][N:13]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:18][CH2:17]2)[CH:35]=[CH:36][CH:37]=1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 178418339Butyllithium

Product 1

HCID 86649625HCID 86649625, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.855 ml of diisopropylamine in 15 ml of tetrahydrofuran was added 2.26 ml of a hexane solution containing 2.66 M n-butyllithium at 0° C., followed by stirring the reaction mixture at 0° C. for 30 minutes. After cooling down to −78° C., a solution of 1.54 g of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate in 5 ml of tetrahydrofuran was added to the reaction mixture, and the resultant mixture was stirred at −78° C. for 30 minutes. A solution of 1.00 g of 2-bromo-6-(bromomethyl)pyridine in 5 ml of tetrahydrofuran was added to the reaction mixture, followed by stirring the reaction mixture at −78° C. for 2 hours. To the reaction mixture was added saturated aqueous ammonium chloride solution, followed by extracting with ethyl acetate. The resulting ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−2/1) to give the title compound as a yellow oil.

Workup

  1. temperatureAfter cooling down to −78° C.
  2. stirringby stirring the reaction mixture at −78° C. for 2 hours
  3. extractionby extracting with ethyl acetate
  4. dry with materialThe resulting ethyl acetate solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−2/1)

Sources & evidence

ORD record
ord-e0d52fcf95b74e7883427860c2098790
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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