(3E)-4-[(1S,3R)-3-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-1,2,3,4-tetrahydro-1-methyl-5-isoquinolinyl]-2-methyl-3-buten-2-ol → 4-((1S,3R)-3-(((tert-Butyldimethylsilyl)oxy)methyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-2-methylbutan-2-ol

HRID 1854561Notes

Reaction equation

HRID 1854561 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2/[CH:20]=[CH:21]/[C:22]([CH3:25])([OH:24])[CH3:23])[C@H:12]([CH3:26])[NH:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)C.[Pd].C(OCC)(=O)C>[Si:1]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:20][CH2:21][C:22]([CH3:25])([OH:24])[CH3:23])[C@H:12]([CH3:26])[NH:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 131732505(3E)-4-[(1S,3R)-3-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-1,2,3,4-tetrahydro-1-methyl-5-isoquinolinyl]-2-methyl-3-buten-2-ol

Product 1

HCID 1236252274-((1S,3R)-3-(((tert-Butyldimethylsilyl)oxy)methyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-2-methylbutan-2-olYield 95.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Add a solution of (E)-4-[(1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-2-methyl-but-3-en-2-ol (68 g, 168.83 mmol) in ethanol (816 mL) to a pressure hydrogenation vessel and add 5% palladium on activated carbon (35.83 g, 16.84 mmol). Purge the vessel with hydrogen gas, pressurise to 470 kPa of hydrogen gas and stir at 25° C. After 16 hours, vent the vessel and filter the reaction mixture through diatomaceous earth. Wash the diatomaceous earth with ethyl acetate and concentrate the filtrate under reduced pressure to give an oil. Dissolve the oil in ethyl acetate (1 L) and concentrate under reduced pressure to give the title compound (64 g, 161 mmol). MS (m/z): 378.2 (M+1).

Workup

  1. customPurge the vessel with hydrogen gas, pressurise to 470 kPa of hydrogen gas
  2. filtrationfilter the reaction mixture through diatomaceous earth
  3. washWash the diatomaceous earth with ethyl acetate
  4. concentrationconcentrate the filtrate under reduced pressure
  5. customto give an oil
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-5faa5525ace849f8b47360e10da7bc3a
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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