Toluene → N-((S)-6-allyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

HRID 1913817노트

반응식

HRID 1913817 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13](=[O:27])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)=[CH:16][CH:15]=1)[CH2:6][CH2:5]2.[C:28]1(C)[CH:33]=CC=C[CH:29]=1.C([Sn](CCCC)(CCCC)CCCC)C=C>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:33]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13](=[O:27])[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)=[CH:18][CH:19]=1)[CH2:6][CH2:5]2)[CH:28]=[CH2:29]

참가 물질

6

반응물 3

HCID 1140TolueneHCID 90628AllyltributylstannaneHCID 67545579N-((S)-6-Bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

생성물 1

HCID 67544894N-((S)-6-allyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of N-((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (1.00 g), toluene (10 ml), Pd(PPh3)4 (26.7 mg) and allyltributyltin (2.46 g) was boiled at reflux for 5 hours. The cooled reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was washed with sodium chloride solution, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel. The product was thus obtained with the molecular weight of 391.51 (C25H29NO3); MS (ESI): 392 (M+H+).

후처리

  1. temperatureat reflux for 5 hours
  2. customThe cooled reaction mixture
  3. washwashed with water
  4. washThe organic phase was washed with sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel
  8. customThe product was thus obtained with the molecular weight of 391.51 (C25H29NO3)

출처 및 근거

ORD 기록
ord-384f8a2aab5d41d2932307cff9952c5f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609731B2

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