1,1-dimethylethyl 6-cyano-1-[(2E)-4-(ethyloxy)-4-oxo-2-buten-1-yl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate → 1,1-Dimethylethyl 6-cyano-1-[4-(ethyloxy)-4-oxobutyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

HRID 2383315Notes

Reaction equation

HRID 2383315 reaction equation
[C:1]([C:3]1[C:4]([CH3:28])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13]/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:7][CH2:6]2)#[N:2]>C(O)C.[Pd]>[C:1]([C:3]1[C:4]([CH3:28])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:7][CH2:6]2)#[N:2]

Participants

4

Reactant 1

HCID 595910891,1-dimethylethyl 6-cyano-1-[(2E)-4-(ethyloxy)-4-oxo-2-buten-1-yl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Product 1

HCID 595910941,1-Dimethylethyl 6-cyano-1-[4-(ethyloxy)-4-oxobutyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylateYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1,1-dimethylethyl 6-cyano-1-[(2E)-4-(ethyloxy)-4-oxo-2-buten-1-yl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 25; 530 mg, 1.38 mmol) in ethanol (20 ml) under nitrogen was added palladium on carbon (106 mg, 0.100 mmol). The resulting mixture was stirred under an atmosphere of hydrogen (1 bar) for 105 min. The catalyst was filtered off through Celite® and the filtrate concentrated in vacuo to give the title compound (530 mg).

Workup

  1. filtrationThe catalyst was filtered off through Celite®
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-55c1ec0fc6b64459a153d677111b267e
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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