Acetic Acid → 2-Acetylamino-2-acetylaminomethyl-bicyclo[3.2.1]octane

HRID 483316Notes

Reaction equation

HRID 483316 reaction equation
[C:1]([NH:4][C:5]1([C:13]#[N:14])[CH2:11][CH2:10][CH:9]2[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])[CH2:11][CH2:10][CH:9]2[CH2:12][CH:6]1[CH2:7][CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 197520962-Acetylamino-2-cyano-bicyclo[3.2.1]octane

Product 1

HCID 197520812-Acetylamino-2-acetylaminomethyl-bicyclo[3.2.1]octane

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[3.2.1]octane (9 g), in the form of the mixture of the exo and endo racemates in a ratio of (8/1), in acetic acid (140 cc) and acetic anhydride (8.8 cc), in the presence of Adams platinum oxide (0.9 g); by chromatographing the residue from the evaporation on a column 5.5 cm in diameter containing silica gel (250 g), eluting with a mixture of ethyl acetate and ethanol (75/25 by volume) and collecting fractions of 100 cc. The fractions between 1400 and 3100 cc are concentrated to dryness. 2-Acetylamino-2-acetylaminomethyl-bicyclo[3.2.1]octane (9.75 g) is thus obtained in the form of fine white crystals which melt at 92°-3° C.

Workup

  1. customby chromatographing the residue from the evaporation on a column 5.5 cm in diameter
  2. additioncontaining silica gel (250 g)
  3. washeluting with a mixture of ethyl acetate and ethanol (75/25 by volume)
  4. customcollecting fractions of 100 cc
  5. concentrationThe fractions between 1400 and 3100 cc are concentrated to dryness

Sources & evidence

ORD record
ord-a9a0b9ccbb67459f8a1ff48b65bb44f0
Source dataset
uspto-grants-1993_07
Patent number
US05225207

Reaction notes

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