Diazoethane → HCID 19757987, compound

HRID 1587377Notes

Reaction equation

HRID 1587377 reaction equation
[C:1]([CH:3]1[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1)#[N:2].[C:11]([OH:16])(=[O:15])[C:12]([OH:14])=[O:13].C[N:18]1[N:22]=N[C:20]([CH:23]2C3CCN(CC3)C2)=[N:19]1.[N+](=CC)=[N-]>>[C:11]([OH:16])(=[O:15])[C:12]([OH:14])=[O:13].[CH2:20]([N:19]1[N:18]=[N:22][C:1]([CH:3]2[CH:8]3[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]3)[CH2:4]2)=[N:2]1)[CH3:23]

Participants

4

Reactant 3

HCID 70695DiazoethaneHCID 1428651-Azabicyclo(2.2.2)octane-3-carbonitrileHCID 19758000HCID 19758000, compound

Product 1

HCID 19757987HCID 19757987, compound

Procedure

This compound was prepared from (±) 3-cyano-1-azabicyclo[2.2.2]octane (EP-A-0 261 763, Description 1) in a similar manner to the compound of Example 2 using an ethereal solution of diazoethane prepared from N-nitroso-N-ethyl urea1,2. The resulting oil was purified by column chromatography using neutral alumina and eluting with 2% MeOH/EtOAc. 1H NMR indicated that the mixture contained a 12:1 ratio of the 2-ethyl isomer to 1-ethyl isomer and this mixture (100 mg, 17%) was crystallised and the title compound E9 recrystallised from methanol/diethyl ether as the oxalate salt (containing 8% of the 1-ethyl isomer).

Workup

  1. customprepared from N-nitroso-N-ethyl urea1,2
  2. customThe resulting oil was purified by column chromatography
  3. washeluting with 2% MeOH/EtOAc
  4. customthis mixture (100 mg, 17%) was crystallised
  5. customthe title compound E9 recrystallised from methanol/diethyl ether as the oxalate salt (containing 8% of the 1-ethyl isomer)

Sources & evidence

ORD record
ord-6e44745b98294840bdcabe5c34a48ce3
Source dataset
uspto-grants-1993_06
Patent number
US05217975

Reaction notes

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