{1-[2-(4-Benzyloxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester → {1-[2-(4-Hydroxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

HRID 2279428Notes

Reaction equation

HRID 2279428 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[N:19][C:20]3[C:25]([C:26]=2[O:27]CC2C=CC=CC=2)=[N:24][C:23]([O:35][CH3:36])=[CH:22][CH:21]=3)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6](=[O:37])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[N:19][C:20]3[C:25]([C:26]=2[OH:27])=[N:24][C:23]([O:35][CH3:36])=[CH:22][CH:21]=3)[CH2:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 66746573{1-[2-(4-Benzyloxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

Product 1

HCID 178487971{1-[2-(4-Hydroxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl esterYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on activated carbon (3.45 g, 3.29 mmol, 0.18 eq) is added at room temperature to a stirred solution of {1-[2-(4-benzyloxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester (9.3 g, 18.28 mmol, 1.0 eq) in methanol (100 mL). The mixture is hydrogenated for 7 hours, then filtered through decalite. Solvent is removed to afford {1-[2-(4-hydroxy-6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester as an off-white solid (7.1 g, 91% yield).

Workup

  1. filtrationfiltered through decalite
  2. customSolvent is removed

Sources & evidence

ORD record
ord-4e3b01663ae64cc1bd6ffa71ace44517
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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