Pyridine → HCID 21478769, compound

HRID 1928869Notes

Reaction equation

HRID 1928869 reaction equation
[CH:1]([N:4]1[CH:9]2[CH2:10][C:11](=O)[CH2:12][CH:5]1[CH2:6][O:7][CH2:8]2)([CH3:3])[CH3:2].N1C=CC=CC=1.Cl.[NH2:21][OH:22]>C(O)C>[CH:1]([N:4]1[CH:9]2[CH2:10][C:11](=[N:21][OH:22])[CH2:12][CH:5]1[CH2:6][O:7][CH2:8]2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 21478729HCID 21478729, compound

Product 1

HCID 21478769HCID 21478769, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 9-isopropyl-3-oxa-9-aza-bicyclo[3.3.1]nonan-7-one (CAS no: 99189-30-7)(1.25 g, 6.82 mmol) in ethanol (40 mL) and pyridine (0.8 mL, 10.2 mmol) with hydroxylamine hydrochloride (0.5 g, 7.23 mmol) was refluxed for 6 h. Cooled to 23° C., evaporated all volatiles, partitioned the residue between dichloromethane and sodium carbonate solution, reextracted the aqueous layer with tetrahydrofuran/ethyl acetate, all combined organic layers were dried over Na2SO4, filtered and the solvents evaporated to give the title compound as a dark brown solid. (1.0 g, 74%); MS: m/e=199.1 (M+H+).

Workup

  1. customevaporated all volatiles
  2. custompartitioned the residue between dichloromethane and sodium carbonate solution
  3. dry with materialall combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents evaporated

Sources & evidence

ORD record
ord-9a765620467e428790f3b20eb71ed00d
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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