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

HRID 1180692ノート

反応式

HRID 1180692 の反応式
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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 69501896(R)-N-Allyl-N-octanoyl-1-phenylethylamineHCID 178418310HCID 178418310、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-869498c9dc5b4f33801c8c231caa2a25
出典データセット
uspto-grants-2007_10
特許番号
US07282605B2

反応ノート

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