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

HRID 657034Notes

Reaction equation

HRID 657034 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 86635339Phenylmethyl [((3S,4S)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

Product 1

HCID 689665271-{2-[(3S,4S)-3-(Aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-oneYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl [((3S,4S)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate (0.90 g, 1.99 mmol) in MeOH (30 mL) was added catalytic 10% Palladium on carbon (0.20 g) and the resulting solution subjected to H2 at 50 PSI on a Parr shaker. The solution was filtered through a pad of Celite® and concentrated under reduced pressure to give the product (0.571 g, 90%).

Workup

  1. filtrationThe solution was filtered through a pad of Celite®
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e39256848c714ad0ab9f5d91993a9ac5
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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