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

HRID 657046Notes

Reaction equation

HRID 657046 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:32])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:18][C@@H:17]([OH:19])[C@@H:16]([CH2:20][NH:21]C(=O)OCC3C=CC=CC=3)[CH2:15]2)=[N:4][CH:3]=1>[Pd]>[NH2:21][CH2:20][C@@H:16]1[C@H:17]([OH:19])[CH2:18][N:14]([CH2:13][CH2:12][N:9]2[C:10]3[C:5](=[N:4][CH:3]=[C:2]([F:1])[CH:11]=3)[CH:6]=[CH:7][C:8]2=[O:32])[CH2:15]1

Participants

3

Reactant 1

HCID 86635342Phenylmethyl ({(3S,4S)-1-[2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-4-hydroxy-3-pyrrolidinyl}methyl)carbamate

Product 1

HCID 688098161-{2-[(3S,4S)-3-(aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-7-fluoro-1,5-naphthyridin-2(1H)-oneYield 110.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of phenylmethyl ({(3S,4S)-1-[2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-4-hydroxy-3-pyrrolidinyl}methyl)carbamate (1.7 g; 3.85 mmol) was added 10% Pd/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 (1.3 g; 100%).

Workup

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

Sources & evidence

ORD record
ord-c4f3f98e894c4132b90548ab8ec48a14
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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