HCID 59398358, compound → HCID 59397848, compound

HRID 39895Notes

Reaction equation

HRID 39895 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[C:33]([O:38]CC6C=CC=CC=6)[CH:34]=[CH:35][CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:46])[CH2:22][CH2:21]3)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1>[Pd].CO>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[C:33]([OH:38])[CH:34]=[CH:35][CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:46])[CH2:22][CH2:21]3)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 59398358HCID 59398358, compound

Product 1

HCID 59397848HCID 59397848, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 15 mL of a methanol solution containing 309 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-benzyloxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 31 mg of 5% palladium on carbon was added, and stirred at room temperature under hydrogen atmosphere overnight. The insoluble material was filtered off, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; chloroform:methanol=20:1], to give 239 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-hydroxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a pale brown foam.

Workup

  1. additionwas added
  2. filtrationThe insoluble material was filtered off
  3. customthe solvent was removed under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; chloroform:methanol=20:1]

Sources & evidence

ORD record
ord-a17ca4fb36744e7089b06321e9133a8f
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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