Sodium hydride → 4-{[(1R,3S,4S)-3-([tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy)methyl)cyclopentyl]oxy}-3-nitropyridin-2-amine

HRID 1397600Notes

Reaction equation

HRID 1397600 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:14][CH:13]([OH:15])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[NH2:18][C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[C:23](Cl)[CH:22]=[CH:21][N:20]=1>C1COCC1>[Si:1]([O:8][C@@H:11]1[C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:14][C@@H:13]([O:15][C:23]2[CH:22]=[CH:21][N:20]=[C:19]([NH2:18])[C:24]=2[N+:25]([O-:27])=[O:26])[CH2:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 40716944-Chloro-3-nitropyridin-2-amineHCID 771919633-{[(Tert-butyldimethylsilyl)oxy]methyl}cyclopentan-1-ol

Product 1

HCID 667981204-{[(1R,3S,4S)-3-([tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy)methyl)cyclopentyl]oxy}-3-nitropyridin-2-amineYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,3S,4S)-3-f[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanol (0.782 g, 0.00217 mol) in THF (30.0 mL) was added NaH (0.156 g, 0.00650 mol) and the mixture was stirred for 1 h. To this was added 2-amino-4-chloro-3-nitropyridine (0.376 g, 0.00217 mol) and the mixture was stirred overnight. The solution was concentrated and the residue was purified by flash chromatography (25% EtOAc/hexanes) to afford the title compound (0.381 g, 35%) as a yellow solid.

Workup

  1. stirringthe mixture was stirred overnight
  2. concentrationThe solution was concentrated
  3. customthe residue was purified by flash chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bd01f0f83d13403c83f67fede5a2ed1d
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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