HCID 86635370, compound → HCID 68991981, compound

HRID 657146Notes

Reaction equation

HRID 657146 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:33])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][C@H:17]([OH:20])[C@H:16]([CH2:21][NH:22]C(=O)OCC3C=CC=CC=3)[CH2:15]2)=[CH:4][CH:3]=1>CCO.[OH-].[OH-].[Pd+2]>[NH2:22][CH2:21][C@H:16]1[C@@H:17]([OH:20])[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][N:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=3)[CH:6]=[CH:7][C:8]2=[O:33])[CH2:15]1

Participants

4

Reactant 1

HCID 86635370HCID 86635370, compound

Product 1

HCID 68991981HCID 68991981, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of phenylmethyl ({(3R,4S)-1-[2-(7-fluoro-2-oxo-1(2H)-quinolinyl)ethyl]-4-hydroxy-3-piperidinyl}methyl)carbamate (525 mg; 1.16 mmol) in EtOH (100 mL) was added 20% Pd(OH)2/C (100 mg). The mixture was hydrogenated at 1 atm of H2 at ambient temperature for 2 h. The crude product was filtered through Celite, washed with ethanol and concentrated under reduced pressure to obtain the product as a pale yellow oil (356 mg; 96%).

Workup

  1. filtrationThe crude product was filtered through Celite
  2. washwashed with ethanol
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-893e5d561edb4048bcb2e331849214fc
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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