Diisopropylamine → HCID 67745421, compound

HRID 1735414Notes

Reaction equation

HRID 1735414 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([O:17][C:18]([N:20]1[CH2:26][CH2:25][CH2:24][C@H:21]1[CH:22]=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].[Cl-].[NH4+].[C:29]([O:32][CH2:33][CH3:34])(=[O:31])[CH3:30]>O.C1COCC1.CCCCCC>[C:13]([O:17][C:18]([N:20]1[CH2:26][CH2:25][CH2:24][C@H:21]1[CH:22]([OH:23])[CH2:30][C:29]([O:32][CH2:33][CH3:34])=[O:31])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 67745421HCID 67745421, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A 1.6M n-hexane solution (23.5 ml) of n-butyl lithium was added to a THF solution (5 ml) of diisopropyl amine (5.3 ml) under an argon atmosphere at -40° C., and the mixture was stirred for 5 minutes and 30 minutes under ice-cooling. After cooling to -78° C., ethyl acetate (3.7 ml) was dropwise added, and the mixture was stirred for 15 minutes. A THF solution (18 ml) of N-(tert-butoxycarbonyl)-L-prolinal (4.98 g) was dropwise added at -78° C. and the mixture was stirred for 1.5 hours. Saturated ammonium chloride (20 ml) was added, and the reaction mixture was allowed to reach room temperature. The reaction mixture was poured into water, and extracted with ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (eluent: n-hexane-ethyl acetate) to give the title compound (5.73 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 15 minutes
  3. stirringthe mixture was stirred for 1.5 hours
  4. customto reach room temperature
  5. extractionextracted with ether
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9eb4b1721f1e441a947244bb291aa43f
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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