phenylmethyl[((3S)-1-{(2R)-2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-2-hydroxyethyl}-3-pyrrolidinyl)methyl]carbamate → (1R)-2-[(3S)-3-(aminomethyl)-1-pyrrolidinyl]-1-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethanol

HRID 639079Notes

Reaction equation

HRID 639079 reaction equation
C1(COC(=O)[NH:10][CH2:11][C@@H:12]2[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[N:28]=4)[N:23]=[CH:22][C:21]=3[F:32])[OH:19])[CH2:13]2)C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[NH2:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[N:28]=3)[N:23]=[CH:22][C:21]=2[F:32])[OH:19])[CH2:13]1

Participants

4

Reactant 1

HCID 59026240phenylmethyl[((3S)-1-{(2R)-2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-2-hydroxyethyl}-3-pyrrolidinyl)methyl]carbamate

Product 1

HCID 59026145(1R)-2-[(3S)-3-(aminomethyl)-1-pyrrolidinyl]-1-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethanolYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of phenylmethyl[((3S)-1-{(2R)-2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-2-hydroxyethyl}-3-pyrrolidinyl)methyl]carbamate (250 mg, 0.55 mmol) in EtOH (5 mL) was added Pd(OH)2 (20 mg). The suspension was hydrogenated at 1 atm of H2 using a balloon. After 12 h, the mixture was filtered and washed several times with MeOH. The filtrate was concentrated to afford the title compound (175 mg, 100%) as an off-white foam, which was used without further purification: LC/MS (ES) m/e 321 (M+H)+.

Workup

  1. filtrationthe mixture was filtered
  2. washwashed several times with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-74ff9f29c5894168b642a0f9dca52997
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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