(+/-)-Phenylmethyl[(trans-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]carbamate → (+/-)-Trans-4-(aminomethyl)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinol

HRID 639088Notes

Reaction equation

HRID 639088 reaction equation
C1(COC(=O)[NH:10][CH2:11][C@H:12]2[C@H:16]([OH:17])[CH2:15][N:14]([CH2:18][CH2:19][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])[CH2:13]2)C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:10][CH2:11][C@@H:12]1[CH2:13][N:14]([CH2:18][CH2:19][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])[CH2:15][C@H:16]1[OH:17]

Participants

4

Reactant 1

HCID 131728028(+/-)-Phenylmethyl[(trans-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]carbamate

Product 1

HCID 68818112(+/-)-Trans-4-(aminomethyl)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinolYield 102.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (±)-phenylmethyl[(trans-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]carbamate (1.8 g, 3.96 mmole) in MeOH (100 mL) in a round bottom flask was added Pd(OH)2 (˜100 mg). The reaction contents were stirred under a balloon of H2 overnight at RT. The reaction contents were filtered through Celite® (MeOH) and concentrated to give the title compound (1.3 g, quant.) as a light yellow foam: LC-MS (ES) m/e 321 (M+H)+.

Workup

  1. customThe reaction contents
  2. customThe reaction contents
  3. filtrationwere filtered through Celite® (MeOH)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4bcac6bc834b497382065093040d247f
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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