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

HRID 639070Notes

Reaction equation

HRID 639070 reaction equation
C1(COC(=O)[NH:10][CH2:11][C@@H:12]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([O:29][CH3:30])[N:27]=4)[N:22]=[CH:21][C:20]=3[F:31])[CH2:13]2)C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[F:31][C:20]1[CH:21]=[N:22][C:23]2[C:28]([C:19]=1[CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][C@@H:12]([CH2:11][NH2:10])[CH2:13]1)=[N:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2

Participants

4

Reactant 1

HCID 59026091phenylmethyl[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

Product 1

HCID 59026234[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amineYield 76%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate (0.13 g, 0.29 mmole) in MeOH (50 mL) was added Pd(OH)2 (100 mg). The reaction contents were placed under a balloon of H2 and stirred for 18 hours. The reaction contents were filtered through Celite (MeOH) and concentrated under vacuum to give the title compound (66 mg, 76%) as a light yellow oil: LC-MS (ES) m/e 305 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-de3f781d078b411e94a34093a3ec300d
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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