Lithium hydride → [2-(6-Methyl-5-nitro-pyridin-2-yloxy)-ethyl]-propyl-carbamic Acid Tert-Butyl Ester

HRID 390307Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[C:12]([O:16][C:17](=[O:25])[N:18]([CH2:22][CH2:23][OH:24])[CH2:19][CH2:20][CH3:21])([CH3:15])([CH3:14])[CH3:13].[H-].[Li+]>C1(C)C=CC=CC=1>[C:12]([O:16][C:17](=[O:25])[N:18]([CH2:22][CH2:23][O:24][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[N:7]=1)[CH2:19][CH2:20][CH3:21])([CH3:13])([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-chloro-2-methyl-3-nitro-pyridine (1 g, 5.79 mmol), (2-hydroxyethyl)-propyl-carbamic acid tert-butyl ester (1.18 g, 5.79 mmol) and lithium hydride (0.05 g, 6.37 mmol) in toluene (5 ml) was stirred at 90° C. for 4 h. After evaporation of the solvent under reduced pressure the residue was purified by silica gel chromatography with heptane/ethyl acetate (10:0; 8:2; 0:10) as eluent to provide 1.38 g (70.2%) of the product.

Workup

customAfter evaporation of the solvent under reduced pressure the residue
customwas purified by silica gel chromatography with heptane/ethyl acetate (10:0; 8:2; 0:10) as eluent

Sources & evidence

ORD record: ord-829d15ee53bc44dda6cc3e177fe664ed
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383641B2

Reaction notes

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