Hydroxylamine → HCID 15767027, compound

HRID 1492903Notes

Reaction equation

HRID 1492903 reaction equation
NO.[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH:17]([NH2:19])[CH3:18])[CH2:14][CH2:15]O)=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(O)(=O)C.CCCCCC>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:14][CH2:15][NH:19][CH:17]2[CH3:18])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18949782HCID 18949782, compound

Product 1

HCID 15767027HCID 15767027, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

4.2 g (0.018 mol) of the aminoalcohol prepared in (c), 4.69 g (0.018 mol) of triphenylphosphine and 3.1 g (0.018 mol) of diethyl azodicarboxylate were dissolved in 100 mL THF. 2 drops of glacial acetic acid were added and the solution refluxed for two hours. During this time the initially red solution became yellow. On cooling, hexane was added dropwise until precipitation started. The mixture was then cooled in the freezer and the crystalline precipitate filtered off. The solvent was removed under reduced pressure and the residue taken up in chloroform and washed with water. The organic layer was dried with MgSO4, filtered, the solvent evaporated off under reduced pressure and the residue vacuum distilled (130° C. at 2 mm Hg) to afford 3.0 g (77 percent of theoretical) of the crude product in the form of a mobile oil. The NMR and IR spectra of the product were consistent with the expected structure and indicated a mixture of the two possible diastereoisomers were present in a ratio of 3:1.

Workup

  1. temperaturethe solution refluxed for two hours
  2. temperatureOn cooling
  3. temperatureThe mixture was then cooled in the freezer
  4. filtrationthe crystalline precipitate filtered off
  5. customThe solvent was removed under reduced pressure
  6. washwashed with water
  7. dry with materialThe organic layer was dried with MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated off under reduced pressure
  10. distillationthe residue vacuum distilled (130° C. at 2 mm Hg)

Sources & evidence

ORD record
ord-b71442ddc3e54498bfad1c1ceef8d31a
Source dataset
uspto-grants-1994_12
Patent number
US05376659

Reaction notes

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