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

HRID 1086473Notes

Reaction equation

HRID 1086473 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>CO>[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-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of this amine (907 mg) and (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane (745 mg) in 20 ml of methanol was heated at reflux for 39 hours. The reaction mixture was concentrated to dryness and chromatographed on silica gel (95:5:1 CH2Cl2 :MeOH:NH4OH) to give 1.27 g of (R)-α-[[(1,1-dimethyl-2-(2-methyl-1H-indol-3-yl))ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol.

Workup

  1. temperatureat reflux for 39 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customchromatographed on silica gel (95:5:1 CH2Cl2 :MeOH:NH4OH)

Sources & evidence

ORD record
ord-758f1896e35a4cc09ccb40bb094606e3
Source dataset
uspto-grants-1991_07
Patent number
US05030640

Reaction notes

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