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

HRID 1086472Notes

Reaction equation

HRID 1086472 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-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane (0.60 g) and (1,1-dimethyl-2-(5-benzyloxy-1H-indol-3-yl))ethyl amine (1.09 g, 3.55 mmol) in 15 ml of absolute ethanol was heated at reflux for 23 hours under an inert atmosphere. The reaction mixture was concentrated under reduced pressure to give crude product (1.59 g) which was chromatographed on silica gel (95:5:0.5 CH2Cl2 :MeOH:NH4OH) to give 1.27 g of (R)-α-[[(1,1-dimethyl-2-(5-benzyloxy-1H-indol-3-yl))ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol.

Workup

  1. temperatureat reflux for 23 hours under an inert atmosphere
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give crude product (1.59 g) which
  4. customwas chromatographed on silica gel (95:5:0.5 CH2Cl2 :MeOH:NH4OH)

Sources & evidence

ORD record
ord-a40a44be3d15497582e208a9d34baf5e
Source dataset
uspto-grants-1991_07
Patent number
US05030640

Reaction notes

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