Water → 8-Azabicyclo[3.2.1]octan-3-one, 8-acetyl-

HRID 2274943Notes

Reaction equation

HRID 2274943 reaction equation
[CH2:1]1[CH:8]2[NH:9][CH:3]([CH2:4][C:5]([CH2:7]2)=[O:6])[CH2:2]1.Cl.O.C(Cl)Cl.[OH-].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18]>>[C:17]([N:9]1[CH:8]2[CH2:1][CH2:2][CH:3]1[CH2:4][C:5](=[O:6])[CH2:7]2)(=[O:19])[CH3:18]

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 130912188-Azabicyclo[3.2.1]octan-3-one hydrochloride

Product 1

HCID 120767728-Azabicyclo[3.2.1]octan-3-one, 8-acetyl-

Conditions

Temperature
70 °C

Procedure

A suspension of nortropinone hydrochloride (1 g, 6.187 mmol) in acetic anhydride was stirred at 70° C. for 3 h. Water was added, the mixture was boiled for 30 min and cooled down to room temperature. CH2Cl2 and 1N aqueous NaOH was added until pH 9 was reached. The mixture was extracted 2 times with CH2Cl2, the combined organic layers were dried over Na2SO4, filtrated and the solution was evaporated to dryness to give 0.7 g of 8-Acetyl-8-aza-bicyclo[3.2.1]octan-3-one (4a).

Workup

  1. waitthe mixture was boiled for 30 min
  2. temperaturecooled down to room temperature
  3. extractionThe mixture was extracted 2 times with CH2Cl2
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltrated
  6. customthe solution was evaporated to dryness

Sources & evidence

ORD record
ord-cd6c48e11aab4d7f816fcd7ec99992a7
Source dataset
uspto-grants-2015_09
Patent number
US09127001B2

Reaction notes

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