Phenylmethyl ({(3S)-1-[2-(7-fluoro-2-oxo-1(2H)-quinolinyl)ethyl]-3-pyrrolidinyl}methyl)carbamate → 1-{2-[(3S)-3-(Aminomethyl)-1-pyrrolidinyl]ethyl}-7-fluoro-2(1H)-quinolinone

HRID 657059Notes

Reaction equation

HRID 657059 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:31])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][C@@H:16]([CH2:19][NH:20]C(=O)OCC3C=CC=CC=3)[CH2:15]2)=[CH:4][CH:3]=1>CO.[Pd]>[NH2:20][CH2:19][C@@H:16]1[CH2:17][CH2:18][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:31])[CH2:15]1

Participants

4

Reactant 1

HCID 86635345Phenylmethyl ({(3S)-1-[2-(7-fluoro-2-oxo-1(2H)-quinolinyl)ethyl]-3-pyrrolidinyl}methyl)carbamate

Product 1

HCID 688179411-{2-[(3S)-3-(Aminomethyl)-1-pyrrolidinyl]ethyl}-7-fluoro-2(1H)-quinolinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl ({(3S)-1-[2-(7-fluoro-2-oxo-1(2H)-quinolinyl)ethyl]-3-pyrrolidinyl}methyl)carbamate (820 mg, 1.94 mmol) in MeOH (30 mL) was added 5% palladium on carbon (200 mg, 50% by weight with water). The mixture was hydrogenated at 15 psi for 2.5 h, filtered through a pad of Celite®, and concentrated to give a clear oil which darkened and solidified on standing (555 mg, 99%).

Workup

  1. filtrationfiltered through a pad of Celite®
  2. concentrationconcentrated
  3. customto give a clear oil which

Sources & evidence

ORD record
ord-a5378fe089d34e78b511215f693f12bc
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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