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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
ノート
印刷プレビュー

反応式

HRID 1913837 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

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

生成物 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

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
120 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-cd5feefe8de94badae1140eec63401ee
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08609731B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート