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

HRID 639091Notes

Reaction equation

HRID 639091 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][N:14]1[CH2:18][C@H:17]([OH:19])[C@H:16]([CH2:20][NH:21]C(=O)OCC3C=CC=CC=3)[CH2:15]1)=[N:9][C:8]([O:32][CH3:33])=[CH:7][CH:6]=2>CO.[OH-].[OH-].[Pd+2]>[NH2:21][CH2:20][C@H:16]1[CH2:15][N:14]([CH2:13][CH2:12][C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([O:32][CH3:33])[N:9]=3)[N:4]=[CH:3][C:2]=2[F:1])[CH2:18][C@H:17]1[OH:19]

Participants

4

Reactant 1

HCID 131728029(+/-)-Phenylmethyl[(cis-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]carbamate

Product 1

HCID 59026096(3S,4S)-4-(aminomethyl)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinolYield 100.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl(±)-[(cis-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]carbamate (1.57 g, 3.46 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 (1.11 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-26cfe71901b74dccbc4243a9ac074378
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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