Water → (S)-N-tert-butyl-3,3-dimethyl-2-(1-phenylethylimino)-butyramide

HRID 726870Notes

Reaction equation

HRID 726870 reaction equation
[C:1]([NH:5][C:6](=[O:13])[C:7](=O)[C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:14]1([C@@H:20]([NH2:22])[CH3:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C1(C)C=CC=CC=1>[C:1]([NH:5][C:6](=[O:13])[C:7](=[N:22][C@H:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:21])[C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 758181-Phenethylamine, (-)-HCID 13355144N-tert-Butyl-3,3-dimethyl-2-oxobutanamide

Product 1

HCID 54448077(S)-N-tert-butyl-3,3-dimethyl-2-(1-phenylethylimino)-butyramideYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 30.0 g (162 mmol) of N-tert-butyl-3,3-dimethyl-2-oxo-butyramide (D. Seyferth, R. C. Hui, Tetrahedron Lett. 1984, 25, 5251) and 50 g (413 mmol) of (S)-1-phenylethylamine in 150 ml of toluene was boiled under reflux on a water separator for 20 hours. Subsequently, the solvent and excess amine were removed in a vacuum. The residue was treated with 200 ml of hexane at 0° C. and stirred. After filtration of the suspension and concentration in a vacuum the residual oil was distilled. There were obtained 37.2 g (80%) of (S)-N-tert-butyl-3,3-dimethyl-2-(1-phenylethylimino)-butyramide of boiling point 140° C. at 0.3 mbar. [α]=-40.7 (c=1.0, CHCl3).

Workup

  1. customSubsequently, the solvent and excess amine were removed in a vacuum
  2. additionThe residue was treated with 200 ml of hexane at 0° C.
  3. filtrationAfter filtration of the suspension and concentration in a vacuum the residual oil
  4. distillationwas distilled

Sources & evidence

ORD record
ord-239b7e6c7b324a818673d6f0498f1758
Source dataset
uspto-grants-1998_01
Patent number
US05710322

Reaction notes

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