Methyl(3S,4R)-4-{[(benzyloxy)carbonyl]amino}-1-[2-(5,7-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidine-3-carboxylate → Methyl (3S,4R)-4-amino-1-[2-(5,7-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidine-3-carboxylate

HRID 255188Notes

Reaction equation

HRID 255188 reaction equation
C(OC([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[C:25]([F:31])[CH:26]=[C:27]([F:30])[CH:28]=3)[CH:23]=[CH:22][C:21]2=[O:32])[CH2:14][C@@H:13]1[C:33]([O:35][CH3:36])=[O:34])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C@@H:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[C:25]([F:31])[CH:26]=[C:27]([F:30])[CH:28]=3)[CH:23]=[CH:22][C:21]2=[O:32])[CH2:14][C@@H:13]1[C:33]([O:35][CH3:36])=[O:34]

Participants

4

Reactant 1

HCID 66773657Methyl(3S,4R)-4-{[(benzyloxy)carbonyl]amino}-1-[2-(5,7-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidine-3-carboxylate2×

Product 1

HCID 66775175Methyl (3S,4R)-4-amino-1-[2-(5,7-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidine-3-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl (3S,4R)-4-{[(benzyloxy)carbonyl]amino}-1-[2-(5,7-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidine-3-carboxylate (Intermediate 35) (595 mg, 1.19 mmol) in methanol (10 mL) was hydrogenated over palladium on carbon (10%, wet) at normal pressure and room temperature for 30 minutes. It was filtered through a 0.45 μm membrane, washed with methanol and the wash and filtrate were concentrated under reduced pressure to give 395 mg (91%) of the product as a colorless hard foam.

Workup

  1. filtrationIt was filtered through a 0.45 μm membrane
  2. washwashed with methanol
  3. washthe wash
  4. concentrationfiltrate were concentrated under reduced pressure

Sources & evidence

ORD record
ord-43e94d7037794865941efb1a613e616f
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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