Hydrochloric Acid → N-Isopropyloxycarbonyl-N-(2-allyloctanoyl)-(R)-1-phenylethylamine

HRID 1180693Notes

Reaction equation

HRID 1180693 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].[C:28](Cl)(=[O:33])[O:29][CH:30]([CH3:32])[CH3:31].Cl>C1(C)C=CC=CC=1>[CH:30]([O:29][C:28]([N:4]([C@@H:14]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:15])[C:5](=[O:13])[CH:6]([CH2:24][CH:22]=[CH2:23])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:33])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7917Isopropyl chloroformateHCID 69501896(R)-N-Allyl-N-octanoyl-1-phenylethylamineHCID 178418310HCID 178418310, compound

Product 1

HCID 69502054N-Isopropyloxycarbonyl-N-(2-allyloctanoyl)-(R)-1-phenylethylamineYield 78.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 40.0 g (0.14 mol) of (R)-N-allyl-N-octanoyl-1-phenylethylamine in 400 ml of toluene was added dropwise 105 ml (0.17 mol) of tert-butylmagnesium chloride (1.6 M) at room temperature, and the reaction was allowed to proceed at 70° C. for 6 hours. The reaction mixture was cooled to room temperature and, then, 51.0 g (0.42 mol) of isopropyl chlorocarbonate was added, and the reaction was allowed to proceed at room temperature for 15 hours. After completion of the reaction, the reaction mixture was added dropwise to 170 ml of a 1 N aqueous solution of hydrochloric acid in an ice bath. The reaction mixture was extracted with 400 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 52.1 g of a crude product. The crude product was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1) to give 41.0 g of the title compound as a colorless oil (yield 78%, diastereomer ratio (1R,2S):(1R,2R)=80:20).

Workup

  1. waitto proceed at room temperature for 15 hours
  2. customAfter completion of the reaction
  3. extractionThe reaction mixture was extracted with 400 ml of hexane
  4. washthe organic layer was washed with 100 ml of a saturated aqueous solution of sodium chloride
  5. concentrationconcentrated under reduced pressure
  6. customto give 52.1 g of a crude product
  7. customThe crude product was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-2c084fe2dc084fdc8d0652aea68e5b8b
Source dataset
uspto-grants-2007_10
Patent number
US07282605B2

Reaction notes

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