Ethyl orthoformate → 3-(1H-Tetrazol-1-yl)-1-azabicyclo[2.2.2]octane

HRID 1589825Notes

Reaction equation

HRID 1589825 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.[N-:12]=[N+:13]=[N-:14].[Na+].[CH2:16](OC(OCC)OCC)C>C(O)(=O)C>[N:3]1([CH:4]2[CH:9]3[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]3)[CH2:5]2)[CH:16]=[N:14][N:13]=[N:12]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 197853Quinuclidine, 3-amino-, dihydrochloride

Product 1

HCID 156699763-(1H-Tetrazol-1-yl)-1-azabicyclo[2.2.2]octaneYield 60.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 3-aminoquinuclidine dihydrochloride (19.94 g, 0.1 mol), sodium azide (7.8 g, 0.12 mol) and triethylorthoformate (22 mL, 0.15 mol) in glacial acetic acid (50 mL) is heated at an oil bath temperature of 100° C. for 3 hours. The solvent is removed and the oily residue is partitioned between aqueous concentrated potassium carbonate solution and chloroform. The organic layer is dried (potassium carbonate) and concentrated to an oil. The oil is purified by column chromatography (silica gel eluting with chloroform-methanol 8:2) to give 10.82 g of the title compound; mp 83°-84° C. as a white solid.

Workup

  1. customThe solvent is removed
  2. customthe oily residue is partitioned between aqueous concentrated potassium carbonate solution and chloroform
  3. dry with materialThe organic layer is dried (potassium carbonate)
  4. concentrationconcentrated to an oil
  5. customThe oil is purified by column chromatography (silica gel eluting with chloroform-methanol 8:2)

Sources & evidence

ORD record
ord-6e00238067ac4c199e0cec99a7edfdff
Source dataset
uspto-grants-1993_04
Patent number
US05200419

Reaction notes

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