Water → 1,1-Dimethylethyl (1-{3-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]propyl}-4-piperidinyl)carbamate

HRID 15297Notes

Reaction equation

HRID 15297 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[N:29]=3)[N:24]=[CH:23][CH:22]=2)[C:17](OC)=[O:18])[CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:18][CH2:17][CH:16]([C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[N:29]=2)[N:24]=[CH:23][CH:22]=1)[CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:3])([CH3:4])[CH3:1])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57423104Methyl 3-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]propanoate

Product 1

HCID 574231051,1-Dimethylethyl (1-{3-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]propyl}-4-piperidinyl)carbamateYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]propanoate (1.70 g, 3.83 mmol) in tetrahydrofuran (40 ml) at −78° C. was added lithium aluminium hydride (1M in diethyl ether, 4.59 ml, 4.59 mmol). The reaction was then stirred at −78° C. for 0.5 h before water (10 ml), then 2M NaOH solution (10 ml) and finally water (10 ml) was added and the mixture warmed to ambient temperature and then filtered and evaporated. The residue was subjected to column chromatography on silica gel using a 0-5% methanol in dichloromethane gradient affording the desired compound as a white solid (601 mg, 38%).

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-e079338607164a9eac2bc15c19164b47
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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