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

HRID 639076Notes

Reaction equation

HRID 639076 reaction equation
C1(COC(=O)[NH:10][CH2:11][C@@H:12]2[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]([OH:31])[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][CH:20]=3)[CH2:13]2)C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][N:14]([CH2:17][C@H:18]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([O:29][CH3:30])[N:27]=3)[N:22]=[CH:21][CH:20]=2)[OH:31])[CH2:13]1

Participants

4

Reactant 1

HCID 59026170phenylmethyl[((3S)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

Product 1

HCID 59026179(1S)-2-[(3S)-3-(aminomethyl)-1-pyrrolidinyl]-1-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethanolYield 98%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl[((3S)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate (0.24 g, 0.56 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 (0.16 g, 98%) as a light yellow oil: LC-MS (ES) m/e 303 (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-6752390094804c1dada5c5cbbfcce83c
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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