(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane → Tetrazolo[1,5-a]pyridine-6-methanol

HRID 1086471Notes

Reaction equation

HRID 1086471 reaction equation
[N:1]1[N:2]=[N:3][N:4]2[CH:9]=[C:8]([C@@H:10]3C[O:11]3)[CH:7]=[CH:6][C:5]=12>C(O)C>[N:1]1[N:2]=[N:3][N:4]2[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:5]=12

Participants

3

Reactant 1

HCID 13090314(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane

Product 1

HCID 131716944Tetrazolo[1,5-a]pyridine-6-methanolYield 133.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 725 mg (3.55 mmol) of (1,1-dimethyl-2-(5-hydroxy-1H-indol-3-yl))ethyl amine (R. V. Heinzelman, et al., J. Org. Chem., 25, 1548 (1960)) and 598 mg of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane in 15 ml of absolute ethanol was stirred at reflux under nitrogen for 13 hours. The reaction mixture was concentrated under reduced pressure to give 1.05 g of crude product. This material was chromatographed on silica gel (90:10:1 CH2Cl2 :MeOH:NH4OH) to give 927 mg of partially purified material. Preparative TLC on silica gel in the same solvent system (eluted twice) afforded pure (R)-α-[[(1,1-dimethyl-2-(5-hydroxy-1H-indol-3-yl))ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol (741 mg).

Workup

  1. temperatureat reflux under nitrogen for 13 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give 1.05 g of crude product
  4. customThis material was chromatographed on silica gel (90:10:1 CH2Cl2 :MeOH:NH4OH)
  5. customto give 927 mg of partially purified material
  6. washPreparative TLC on silica gel in the same solvent system (eluted twice)

Sources & evidence

ORD record
ord-2fc70dcb3e7443389665a5885ae2316e
Source dataset
uspto-grants-1991_07
Patent number
US05030640

Reaction notes

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