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 1747657Notes

Reaction equation

HRID 1747657 reaction equation
[Si:1]([O:8][C@@H:9]1[C@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:12][C@@H:11]([OH:23])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[NH2:26][C:27]1[C:32]([N+:33]([O-:35])=[O:34])=[C:31](Cl)[CH:30]=[CH:29][N:28]=1>C1COCC1>[Si:1]([O:8][C@@H:9]1[C@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:18])[CH2:12][C@@H:11]([O:23][C:31]2[CH:30]=[CH:29][N:28]=[C:27]([NH2:26])[C:32]=2[N+:33]([O-:35])=[O:34])[CH2:10]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 59671236(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanol

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 35.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,3S,4S)-3-{[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-4977991111f943109b41518cfb879da1
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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