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 1913837Notes

Reaction equation

HRID 1913837 reaction equation
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

Participants

7

Reactant 5

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

Product 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

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
120 °C

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-cd5feefe8de94badae1140eec63401ee
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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