HCID 131732503, compound → HCID 123454564, compound

HRID 1854557Notes

Reaction equation

HRID 1854557 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]([O:24][CH2:25][CH3:26])=[O:23])[C@H:12]([CH3:27])[N:11]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[Pd].C(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]([O:24][CH2:25][CH3:26])=[O:23])[C@H:12]([CH3:27])[N:11]1[C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 131732503HCID 131732503, compound

Product 1

HCID 123454564HCID 123454564, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add 10% palladium on carbon (0.09 g) to a 100 ml Parr bottle. Purge with nitrogen. Add ethanol (5 mL) to wet the catalyst. Add tert-butyl (1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-[(E)-3-ethoxy-3-oxo-prop-1-enyl]-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate (330 mg, 0.67 mmol) as a solution in ethanol (15 mL). Seal the bottle and purge with nitrogen. Purge the vessel with hydrogen and pressurize to 414 kPa of hydrogen. Shake at room temperature for 1.5 hours. Vent and open the vessel. Filter the reaction mixture. Concentrate the filtrate under reduced pressure. Purify the residue by silica gel chromatography, eluting with ethyl acetate:hexanes (0-10% gradient) to give the title compound as a clear colorless oil (252 mg, 0.51 mmol). MS (m/z): 392.2 (M-BOC+1).

Workup

  1. customPurge with nitrogen
  2. customSeal the bottle
  3. custompurge with nitrogen
  4. customPurge the vessel with hydrogen
  5. filtrationFilter the reaction mixture
  6. concentrationConcentrate the filtrate under reduced pressure
  7. customPurify the residue by silica gel chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d06d21d630e944a08e6ac365b20c83c4
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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