Diisopropylamine → HCID 86057202, compound

HRID 1984796Notes

Reaction equation

HRID 1984796 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:23][C:24]([CH3:29])([CH3:28])[C:25](Cl)=[O:26]>O1CCCC1.CCCCCC.CN1CCCN(C)C1=O>[CH2:15]([CH:14]([C:25]([C:24]([CH3:29])([CH3:28])[CH3:23])=[O:26])[C:13]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:17][CH3:18]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 31265Ethyl hexanoateHCID 62493Pivaloyl chlorideHCID 178418339Butyllithium

Product 1

HCID 86057202HCID 86057202, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
-70 °C

Procedure

A solution of diisopropylamine (22.5 mL) in anhydrous tetrahydrofuran (THF, 100 mL) was treated dropwise with 1.6 M solution of butyl lithium in hexane (100 mL) at 20° C. under nitrogen atmosphere, stirred at this temperature for additional 30 min, then cooled down to −70° C., and treated dropwise during 30 min with a solution of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 18.6 g) and ethyl hexanoate (21.1 g) in THF (100 mL). Upon completion of the addition, the reaction mixture was stirred for 45 min at −70° C. and after that treated dropwise at the same temperature with a solution of 2,2-dimethyl-propionyl chloride (19.3 g) in THF (50 mL). The mixture was allowed to slowly warm-up to room temperature and stirred at this temperature overnight. Finally the reaction mixture was quenched by pouring onto a mixture of ice and 10% aqueous hydrochloric acid. The formed organic phase was separated and the aqueous phase was extracted with chloroform. The combined organic phases were thoroughly washed with brine to remove DMPU, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator, and distilled in vacuum to give 21.0 g (63%) of the title compound.

Workup

  1. additionUpon completion of the addition
  2. stirringthe reaction mixture was stirred for 45 min at −70° C.
  3. temperatureto slowly warm-up to room temperature
  4. stirringstirred at this temperature overnight
  5. customFinally the reaction mixture was quenched
  6. additionby pouring onto a mixture of ice and 10% aqueous hydrochloric acid
  7. customThe formed organic phase was separated
  8. extractionthe aqueous phase was extracted with chloroform
  9. washThe combined organic phases were thoroughly washed with brine
  10. customto remove DMPU
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated on a rotary evaporator
  14. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-a2fa0a219e01487d84ae8e1e993fbe6d
Source dataset
uspto-grants-2009_06
Patent number
US07544748B2

Reaction notes

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