Phenylmethyl [((3R,4R)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1(2H)-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]carbamate → 1-{2-[(3R,4R)-3-(Aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-7-(methyloxy)-2(1H)-quinolinone

HRID 657006Notes

Reaction equation

HRID 657006 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:21])[CH2:4][C@H:3]1[CH2:22][NH:23]C(=O)OCC1C=CC=CC=1>[OH-].[OH-].[Pd+2]>[NH2:23][CH2:22][C@H:3]1[C@@H:2]([OH:1])[CH2:6][N:5]([CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:21])[CH2:4]1

Participants

3

Reactant 1

HCID 86635331Phenylmethyl [((3R,4R)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1(2H)-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]carbamate

Product 1

HCID 688159151-{2-[(3R,4R)-3-(Aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-7-(methyloxy)-2(1H)-quinolinoneYield 100%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

To a solution of phenylmethyl [((3R,4R)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1(2H)-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]carbamate (337 mg, 0.746 mmol) was added 20% Pd(OH)2/C, degassed and placed under 1 atm of H2 for 18 h. The reaction mixture was filtered through Celite and concentrated to obtain the title compound as a yellow oil (235 mg, 100%).

Workup

  1. customdegassed
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2d9639bde3c5433d918235653209b977
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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