8-(4-ethoxycarbonylmethyl-2-methoxy-phenyl)-5-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester → Ethyl 2-(4-(5-fluoro-1,2,3,4-tetrahydroisoquinolin-8-yl)-3-methoxyphenyl)acetate

HRID 1773995Notes

Reaction equation

HRID 1773995 reaction equation
C(OC([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[C:14]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:24][C:23]=3[O:34][CH3:35])[CH:15]=[CH:16][C:17]=2[F:21])[CH2:12]1)=O)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[F:21][C:17]1[CH:16]=[CH:15][C:14]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:24][C:23]=2[O:34][CH3:35])=[C:13]2[C:18]=1[CH2:19][CH2:20][NH:11][CH2:12]2

Participants

4

Reactant 1

HCID 896482498-(4-ethoxycarbonylmethyl-2-methoxy-phenyl)-5-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

Product 1

HCID 89648494Ethyl 2-(4-(5-fluoro-1,2,3,4-tetrahydroisoquinolin-8-yl)-3-methoxyphenyl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution under N2 of 8-(4-ethoxycarbonylmethyl-2-methoxy-phenyl)-5-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (770 mg, 1.61 mmol, 1 eq.) in AcOEt (60 mL), palladium on activated carbon (10 wt. %, 80 mg) was added. The flask was evacuated and backfilled with H2 (3×). The black suspension was stirred at r.t. under an H2-atmosphere for 18 hours. The suspension was filtered through Celite, the Celite rinsed with AcOEt. The filtrate was concentrated in vacuo to give ethyl 2-(4-(5-fluoro-1,2,3,4-tetrahydroisoquinolin-8-yl)-3-methoxyphenyl)acetate as an yellow oil. The product was used without further purification.

Workup

  1. customThe flask was evacuated
  2. filtrationThe suspension was filtered through Celite
  3. washthe Celite rinsed with AcOEt
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d3467c15331b464b953126a8af64bfbd
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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