Water → Tert-butyl 6-bromo-2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4'-piperidine]-1'-carboxylate

HRID 83001Notes

Reaction equation

HRID 83001 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([CH2:10][C:11]2([C:24]([O:26]CC)=O)[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:8][C:7]([Br:29])=[CH:6][N:5]=1.O>C1COCC1>[Br:29][C:7]1[CH:8]=[C:9]2[C:4](=[N:5][CH:6]=1)[NH:3][C:24](=[O:26])[C:11]1([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:13][CH2:12]1)[CH2:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 671547861-Tert-butyl 4-ethyl 4-((2-amino-5-bromopyridin-3-yl)methyl)piperidine-1,4-dicarboxylate

Product 1

HCID 57742041Tert-butyl 6-bromo-2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4'-piperidine]-1'-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (201 mg, 5.3 mmol) was added to a solution of 1-tert-butyl 4-ethyl 4-((2-amino-5-bromopyridin-3-yl)methyl)piperidine-1,4-dicarboxylate (1.71 g, 3.87 mmol) suspended in THF (17 mL) at room temperature. The reaction mixture was stirred for 1 hour and then diluted by addition of water (50 mL). The resulting precipitate was filtered and washed with pentane. The title compound was obtained as a beige solid (1.2 g, 78%).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with pentane

Sources & evidence

ORD record
ord-49c1c94e6013497f8559e773825b7aef
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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