tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(6-nitro-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate → tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(6-amino-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

HRID 2193314Notes

Reaction equation

HRID 2193314 reaction equation
[C:1]([O:5][C:6](=[O:41])[N:7]([CH2:30][C:31]1[CH:40]=[CH:39][C:34]2[O:35][CH2:36][CH2:37][O:38][C:33]=2[CH:32]=1)[CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[CH:21][C:22]([N+:26]([O-])=O)=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]2=[O:29])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6](=[O:41])[N:7]([CH2:30][C:31]1[CH:40]=[CH:39][C:34]2[O:35][CH2:36][CH2:37][O:38][C:33]=2[CH:32]=1)[CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[CH:21][C:22]([NH2:26])=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]2=[O:29])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59398061tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(6-nitro-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 59398088tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(6-amino-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 4 mL of a methanol solution containing 200 mg of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(6-nitro-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 20 mg of 10% palladium on carbon was added under nitrogen atmosphere, then stirred under hydrogen atmosphere at room temperature for 2 hours. The insoluble material was filtered off, and the solvent was removed under reduced pressure to afford 180 mg of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(6-amino-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a yellow foam.

Workup

  1. additionwas added under nitrogen atmosphere
  2. filtrationThe insoluble material was filtered off
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5fd2f941e40842e1b80ad6b47e181508
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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