Hydrochloric Acid → n-[(r)-2-Allyloctanoyl]-1-phenylethylamine
Reaction equation
C([N:4]([C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])C=C.[C:22]([Mg]Cl)(C)([CH3:24])[CH3:23].Cl>C1(C)C=CC=CC=1>[CH2:24]([C@@H:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:5]([NH:4][CH:14]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:15])=[O:13])[CH:22]=[CH2:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 24.0 g (83.0 mmol) of (R)-N-allyl-N-octanoyl-1-phenylethylamine in 240 ml of toluene was added dropwise 61.5 ml (98.0 mmol) of tert-butylmagnesium chloride (1.6 M) at room temperature and, after completion of the addition, the reaction was allowed to proceed at 70° C. for 6 hours. After completion of the reaction, the reaction mixture was added dropwise to 240 ml of 1 N aqueous hydrochloric acid on an ice bath. The resulting mixture was extracted with 300 ml of hexane, and the organic layer was washed with 100 ml of a saturated aqueous solution of sodium chloride and then concentrated under reduced pressure to give 25.0 g of a crude product. The crude product was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1) to give 13.1 g (76%, (1R,2S):(1R,2R)=80:20) of N-[(R)-2-allyloctanoyl]-1-phenylethylamine.
Workup
- additionafter completion of the addition
- customAfter completion of the reaction
- extractionThe resulting mixture was extracted with 300 ml of hexane
- washthe organic layer was washed with 100 ml of a saturated aqueous solution of sodium chloride
- concentrationconcentrated under reduced pressure
- customto give 25.0 g of a crude product
- customThe crude product was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1)
Sources & evidence
- ORD record
- ord-869498c9dc5b4f33801c8c231caa2a25
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07282605B2
Reaction notes
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