Tert-Butyl nitrite → HCID 21201855, compound

HRID 1979290Notes

Reaction equation

HRID 1979290 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][CH2:9][N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12][C:11]1=[O:27].[N:28](OC(C)(C)C)=[O:29]>C1(C)C=CC=CC=1>[CH3:7][O:8][CH2:9][N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH:12]([NH:28][OH:29])[C:11]1=[O:27]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 21201664HCID 21201664, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21201855HCID 21201855, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Potassium tert-butoxide (57.8 g) was added to 1-methoxymethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (29.1 g) in absolute toluene (1 litter) at 0° C. The resultant mixture was stirred for 30 minutes at 0° C., and tert-butyl nitrite (31.9 g) was added thereto, followed by stirring for 18 hours at room temperature. Ice-water was added to the reaction mixture for separation of layers, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=25:1), to thereby obtain 22.8 g of the title compound as a light brown oily substance (yield: 71.1%).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=25:1)

Sources & evidence

ORD record
ord-8c33612351b14581b25ed73c638836da
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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