(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane → HCID 14988400, compound

HRID 2051495Notes

Reaction equation

HRID 2051495 reaction equation
[N:1]1[N:2]=[N:3][N:4]2[CH:9]=[C:8]([C@@H:10]3[CH2:12][O:11]3)[CH:7]=[CH:6][C:5]=12.[CH3:13][C:14]1([NH2:18])[CH2:17][CH2:16][CH2:15]1>C(O)C>[CH3:13][C:14]1([NH:18][CH2:12][C@@H:10]([C:8]2[CH:7]=[CH:6][C:5]3[N:4]([N:3]=[N:2][N:1]=3)[CH:9]=2)[OH:11])[CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 13090314(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxiraneHCID 14988399(1-Methylcyclobutyl)amine

Product 1

HCID 14988400HCID 14988400, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 375 mg (2.31 mmol) of (R)-2-(tetrazolo [1,5-a]pyrid-6-yl)oxirane and 972 mg (11.42 mmol) of (1-methylcyclobutyl)amine [J. Am. Chem. Soc., 83, 2723 (1961)] in 0.9 ml of absolute ethanol was heated at 70° C. for 3 hours with stirring under nitrogen. The reaction mixture was then concentrated to dryness (wt. 547 mg) and the residue purified by preparative Tlc on silica gel (95:5:1 methylene chloride:methanol:conc. ammonium hydroxide) to give 402 mg of product.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness (wt. 547 mg)
  2. customthe residue purified by preparative Tlc on silica gel (95:5:1 methylene chloride:methanol:conc. ammonium hydroxide)

Sources & evidence

ORD record
ord-03a889b75d8e4e7da1cb922c4217bf99
Source dataset
uspto-grants-1991_05
Patent number
US05019578

Reaction notes

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