Pyridine → HCID 86634178, compound

HRID 1928799Notes

Reaction equation

HRID 1928799 reaction equation
[CH:1]1([N:4]2[CH:9]3[CH2:10][CH2:11][CH:5]2[CH2:6][C:7](=O)[CH2:8]3)[CH2:3][CH2:2]1.N1C=CC=CC=1.Cl.[NH2:20][OH:21]>C(O)C.C([O-])([O-])=O.[Na+].[Na+]>[CH:1]1([N:4]2[CH:9]3[CH2:10][CH2:11][CH:5]2[CH2:6][C:7](=[N:20][OH:21])[CH2:8]3)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 204824738-Cyclopropyl-8-Azabicyclo(3.2.1)octan-3-one

Product 1

HCID 86634178HCID 86634178, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 8-cyclopropyl-8-aza-bicyclo[3.2.1]octan-3-one (CAS no: 60206-33-9) (17.86 g, 108.08 mmol) in ethanol (500 mL) with pyridine (13.05 mL, 162.1 mmol) and hydroxylamine hydrochloride (9.764 g, 140.51 mmol) was refluxed overnight. Cooled to 23° C., filtered off, washed with ethanol and ether and dried in vacuum to give a white solid, which was suspended in 200 mL sat. Na2CO3 solution and extracted 3 times with dichloromethane, the combined organic layers were dried over Na2SO4, filtered off and evaporated totally, dried in high vacuum to give the title compound as white crystals (16.3 g, 84%); MS: m/e=181.2 (M+H+).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationfiltered off
  3. washwashed with ethanol and ether
  4. customdried in vacuum
  5. customto give a white solid, which
  6. extractionextracted 3 times with dichloromethane
  7. dry with materialthe combined organic layers were dried over Na2SO4
  8. filtrationfiltered off
  9. customevaporated totally
  10. customdried in high vacuum

Sources & evidence

ORD record
ord-370e03321b09404989c4483bb8ad8e4e
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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