Acetic Acid → HCID 19752084, compound

HRID 483320Notes

Reaction equation

HRID 483320 reaction equation
[C:1]([NH:4][C:5]1([C:13]#[N:14])[CH2:10][CH:9]2[CH2:11][CH2:12][CH:6]1[CH2:7][CH2:8]2)(=[O:3])[CH3:2].[C:15](O)(=[O:17])[CH3:16]>C(OC(=O)C)(=O)C.[Pt]=O>[C:1]([NH:4][C:5]1([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[CH2:10][CH:9]2[CH2:11][CH2:12][CH:6]1[CH2:7][CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 19752080HCID 19752080, compound

Product 1

HCID 19752084HCID 19752084, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 7918Acetic AnhydrideSolvent

Procedure

The procedure is as in Example 1, but starting from 2-acetylamino-2-cyano-bicyclo[2.2.2]octane (5.8 g) in acetic acid (100 cc) and acetic anhydride (5.6 cc) in the presence of Adams platinum oxide (0.6 g); chromatographing the residue from the evaporation on a column 5.5 cm in diameter containing silica gel (200 g), eluting with a mixture of ethyl acetate and ethanol (75/25 by volume) and collecting fractions of 50 cc. The fractions between 800 and 1750 cc are concentrated to dryness; 2-acetylamino-2-acetylaminomethyl-bicyclo[2.2.2]octane (5.45 g) is thus obtained in the form of a pale yellow viscous oil.

Workup

  1. customchromatographing the residue from the evaporation on a column 5.5 cm in diameter
  2. additioncontaining silica gel (200 g)
  3. washeluting with a mixture of ethyl acetate and ethanol (75/25 by volume)
  4. customcollecting fractions of 50 cc
  5. concentrationThe fractions between 800 and 1750 cc are concentrated to dryness

Sources & evidence

ORD record
ord-030bff23ff8845008751a57d473c95d1
Source dataset
uspto-grants-1993_07
Patent number
US05225207

Reaction notes

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