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Toluene → (S)-6-{1-oxo-6-[(S)-1-(tetrahydrofuran-2-yl)methoxy]-3,4-dihydro-1H-isoquinolin-2-yl}-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

HRID 1913837
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인쇄 미리보기

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HRID 1913837 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([N:12]1[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH2:23][C@@H:24]4[CH2:28][CH2:27][CH2:26][O:25]4)[CH:18]=3)[C:13]1=[O:29])[CH2:6][CH2:5]2.C(P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)CCC.CN(CCN(C)C)C.C1(C)C=CC=CC=1.[C:70](OCC)(=[O:72])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:29]=[C:13]1[C:14]2[C:19](=[CH:18][C:17]([O:22][CH2:23][C@@H:24]3[CH2:28][CH2:27][CH2:26][O:25]3)=[CH:16][CH:15]=2)[CH2:20][CH2:21][N:12]1[C@H:7]1[CH2:6][CH2:5][C:4]2[CH:3]=[C:2]([CH:70]=[O:72])[CH:11]=[CH:10][C:9]=2[CH2:8]1
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참가 물질

7

반응물 5

HCID 1140TolueneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8857Ethyl AcetateHCID 11371790Bis(adamantan-1-yl)(butyl)phosphaneHCID 67545250HCID 67545250, 화합물

생성물 1

HCID 86645830(S)-6-{1-oxo-6-[(S)-1-(tetrahydrofuran-2-yl)methoxy]-3,4-dihydro-1H-isoquinolin-2-yl}-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

반응 조건

온도
120 °C

실험 절차

A mixture of 2-((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-6-[(S)-1-(tetra-hydrofuran-2-yl)methoxy]-3,4-dihydro-2H-isoquinolin-1-one (1.10 g), palladium(II) acetate (16.2 mg), butyldi-1-adamantylphosphine (77 mg), TMEDA (0.27 ml) and toluene (22 ml) was heated to 120° C. in an autoclave under a hydrogen/carbon monoxide atmosphere for 14 hours. The cooled reaction mixture was diluted with ethyl acetate and washed first with dilute hydrochloric acid and then with sodium hydrogen carbonate solution. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC. The product was thus obtained with the molecular weight of 405.50 (C25H27NO4); MS (ESI): 406 (M+H+).

후처리

  1. customThe cooled reaction mixture
  2. washwashed first with dilute hydrochloric acid
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC
  6. customThe product was thus obtained with the molecular weight of 405.50 (C25H27NO4)

출처 및 근거

ORD 기록
ord-cd5feefe8de94badae1140eec63401ee
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08609731B2

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