HCID 118353189, compound → HCID 118353182, compound

HRID 1773992Notes

Reaction equation

HRID 1773992 reaction equation
C(OC([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[C:14]([C:22]3[CH:27]=[C:26]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:25]=[CH:24][C:23]=3[O:34][CH:35]([CH3:37])[CH3:36])[CH:15]=[CH:16][C:17]=2[F:21])[CH2:12]1)=O)C1C=CC=CC=1>CCO.[Pd]>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][C:26]1[CH:25]=[CH:24][C:23]([O:34][CH:35]([CH3:37])[CH3:36])=[C:22]([C:14]2[CH:15]=[CH:16][C:17]([F:21])=[C:18]3[C:13]=2[CH2:12][NH:11][CH2:20][CH2:19]3)[CH:27]=1)[CH3:33]

Participants

4

Reactant 1

HCID 118353189HCID 118353189, compound

Product 1

HCID 118353182HCID 118353182, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-(5-ethoxycarbonylmethyl-2-isopropoxy-phenyl)-5-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (1.65 g, 3.17 mmol, 1 eq.) in EtOH (15.5 mL) under N2, palladium on activated carbon (10 wt. %, 165 mg) was added. The flask was carefully evacuated and refilled with H2 (3×). The black suspension was stirred at r.t. under an H2-atmosphere for 24 hours and further at 50° C. for 18 hours. The black suspension was filtered through Celite. The Celite was rinsed with EtOH. The filtrate was concentrated in vacuo. The residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, AcOEt to (AcOEt+10% NEt3) to yield the title compound as a colorless oil.

Workup

  1. customThe flask was carefully evacuated
  2. additionrefilled with H2 (3×)
  3. filtrationThe black suspension was filtered through Celite
  4. washThe Celite was rinsed with EtOH
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by flashmaster (column

Sources & evidence

ORD record
ord-e435dde95eee49e8ae5d8d0d87506bd8
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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