Hydrochloric Acid → n-[(r)-2-Allyloctanoyl]-1-phenylethylamine

HRID 1180692노트

반응식

HRID 1180692 반응식
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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 69501896(R)-N-Allyl-N-octanoyl-1-phenylethylamineHCID 178418310HCID 178418310, 화합물

생성물 1

HCID 69502035n-[(r)-2-Allyloctanoyl]-1-phenylethylamine수율 76%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  1. additionafter completion of the addition
  2. customAfter completion of the reaction
  3. extractionThe resulting mixture was extracted with 300 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 25.0 g of a crude product
  7. customThe crude product was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-869498c9dc5b4f33801c8c231caa2a25
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282605B2

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