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

HRID 2193324Notes

Reaction equation

HRID 2193324 reaction equation
CO.[C:3]([O:7][C:8](=[O:48])[N:9]([CH:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][N:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([O:39]CC3C=CC=CC=3)=[CH:31][C:30]2=[O:47])[CH2:23][CH2:22]1)[CH2:10][C:11]1[CH:20]=[CH:19][C:14]2[O:15][CH2:16][CH2:17][O:18][C:13]=2[CH:12]=1)([CH3:6])([CH3:5])[CH3:4]>[Pd].O1CCCC1>[C:3]([O:7][C:8](=[O:48])[N:9]([CH2:10][C:11]1[CH:20]=[CH:19][C:14]2[O:15][CH2:16][CH2:17][O:18][C:13]=2[CH:12]=1)[CH:21]1[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][N:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([OH:39])=[CH:31][C:30]2=[O:47])[CH2:25][CH2:26]1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 887MethanolHCID 59397821HCID 59397821, compound

Product 1

HCID 59397962tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-hydroxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 130 mL methanol and 10 mL tetrahydrofuran containing 1.76 g of tert-butyl(1-(2-(4-benzyloxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate, 0.86 g of 5% palladium on carbon was added, and stirred under hydrogen atmosphere for 3.5 hours. The insoluble material was filtered off, and the solvent was removed under reduced pressure to afford 1.48 g of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-hydroxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a white solid.

Workup

  1. filtrationThe insoluble material was filtered off
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f18164aca7ed4bf4bfd522e101bebd0d
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

Loading…