Water → Methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-imidazole-5-carboxylate

HRID 1762047Notes

Reaction equation

HRID 1762047 reaction equation
N(OC(C)(C)C)=O.[CH2:8]1[CH:21]2[CH:12]([CH2:13][C:14]3[C:19]([CH:20]2[N:22]2[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25](N)[N:24]=[CH:23]2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][CH2:10][CH2:9]1.O>CN(C)C=O>[CH2:8]1[CH:21]2[CH:12]([CH2:13][C:14]3[C:19]([CH:20]2[N:22]2[C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][N:24]=[CH:23]2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 23050704methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-4-amino-1H-imidazole-5-carboxylate

Product 1

HCID 20041828Methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-imidazole-5-carboxylateYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4.3 Parts of 1,1-dimethylethyl nitrite were dissolved in 40 ml N,N-dimethylformamide and heated to +60° C. A solution of 8 parts of methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-4-amino-1H-imidazole-5-carboxylate in 50 ml N,N-dimethylformamide was dropwise added at +60° C. After 1.5 hour the solution was poured into water and extracted with ethyl acetate. The organic phase was dried with Na2SO4, filtered and concentrated. The resulting 8.5 parts of crude material were chromatographed on a silica gel column with an ethyl acetate/hexane mixture (1:1). 2.9 Parts (38%) of methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-imidazole-5-carboxylate, mp. 151°-152° C. (compound 2.2), were obtained. According to 1H-NMR the product consists of an epimeric mixture of 2 isomers.

Workup

  1. temperatureheated to +60° C
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting 8.5 parts of crude material were chromatographed on a silica gel column with an ethyl acetate/hexane mixture (1:1)

Sources & evidence

ORD record
ord-9e0a618f77904eed8c659eaafb0d012b
Source dataset
uspto-grants-1989_05
Patent number
US04830664

Reaction notes

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