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 39945Notes

Reaction equation

HRID 39945 reaction equation
CO.C([O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([N:29]([CH2:37][C:38]3[CH:47]=[CH:46][C:41]4[O:42][CH2:43][CH2:44][O:45][C:40]=4[CH:39]=3)[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25][CH2:24]2)[C:13](=[O:48])[CH:12]=1)C1C=CC=CC=1>[Pd].O1CCCC1>[O:42]1[C:41]2[CH:46]=[CH:47][C:38]([CH2:37][N:29]([CH:26]3[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][N:14]4[C:15]5[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=5)[C:11]([OH:10])=[CH:12][C:13]4=[O:48])[CH2:24][CH2:25]3)[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:39][C:40]=2[O:45][CH2:44][CH2:43]1

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-2cf257d263a14cea93d6696ea3f3e95f
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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