Diisopropylamine → HCID 53800227, compound

HRID 1075444Notes

Reaction equation

HRID 1075444 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[C:13]([O:16][CH2:17][CH3:18])(=[O:15])[CH3:14].[N:19]12[CH2:25][CH:22]([CH2:23][CH2:24]1)[C:21](=[O:26])[CH2:20]2>O1CCCC1>[CH2:17]([O:16][C:13](=[O:15])[CH2:14][C:21]1([OH:26])[CH:22]2[CH2:25][N:19]([CH2:24][CH2:23]2)[CH2:20]1)[CH3:18]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 108554071-Azabicyclo[2.2.1]heptan-3-oneHCID 178418339Butyllithium

Product 1

HCID 53800227HCID 53800227, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (-78° C.) solution of diisopropylamine (2.65 ml, 0.0203 moles) in tetrahydrofuran (150 ml) was added 2.5M n-BuLi in hexanes (8.1 ml, 0.0203 moles) dropwise over one minute. After ten minutes, ethyl acetate (1.97 ml, 0.0203 moles) was added dropwise over one minute. After a further ten minutes, 1-azabicyclo[2.2.1]heptan-3-one (1.5 g, 0.0135 moles, prepared by the method of J Chem Soc, Chem Commun, 1618, 1988) in tetrahydrofuran (25 ml) was added dropwise over five minutes. After twenty five minutes, the cold bath was removed and the mixture was allowed to warm to ambient temperature. To this mixture was added water (100 ml) followed by chloroform (250 ml). The organic layer was separated and the aqueous layer was extracted with chloroform (100 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give the subtitle compound (1.12 g).

Workup

  1. waitAfter ten minutes
  2. waitAfter a further ten minutes
  3. additionwas added dropwise over five minutes
  4. waitAfter twenty five minutes
  5. customthe cold bath was removed
  6. additionTo this mixture was added water (100 ml)
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with chloroform (100 ml)
  9. dry with materialThe combined organic extracts were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa6fdca64cb84bb4a7c1feb1a6fdf2c5
Source dataset
uspto-grants-1999_05
Patent number
US05902814

Reaction notes

Loading…