phenylmethyl [((3R,4R)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate → 1-{2-[(3R,4R)-3-(Aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one

HRID 657008Notes

Reaction equation

HRID 657008 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[N: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>CO.[Pd]>[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](=[N: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

4

Reactant 1

HCID 86635332phenylmethyl [((3R,4R)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

Product 1

HCID 689925731-{2-[(3R,4R)-3-(Aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl [((3R,4R)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate (0.76 g, 1.68 mmol) in MeOH (10 mL) was added 10% Palladium on carbon (0.20 g) and the resulting solution subjected to H2 at 20 PSI on a Parr shaker for 1 hour. No reaction was observed. The solution was then subjected to H2 at 50 PSI on a Parr shaker. The solution was filtered through a pad of Celite® and concentrated under reduced pressure (0.408 g, 76%).

Workup

  1. filtrationThe solution was filtered through a pad of Celite®
  2. concentrationconcentrated under reduced pressure (0.408 g, 76%)

Sources & evidence

ORD record
ord-5161f9f27b15425e84ad06317c7044c0
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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