Hydrogen Peroxide → HCID 67031802, compound

HRID 920592Notes

Reaction equation

HRID 920592 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[O:21][CH2:20][CH2:19][N:18]([CH2:22][CH2:23][OH:24])[CH2:17]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].N1C=NN=N1.CC#N.C(N(C(C)C)[P:37]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])(C)C.[OH:51]O>C1COCC1.C(Cl)Cl>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[O:21][CH2:20][CH2:19][N:18]([CH2:22][CH2:23][O:24][P:37](=[O:51])([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])[O:43][C:44]([CH3:45])([CH3:46])[CH3:47])[CH2:17]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 6342AcetonitrileHCID 853005Di-tert-butyl N,N-DiisopropylphosphoramiditeHCID 51002214HCID 51002214, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 67031802HCID 67031802, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[2-(4-octyloxy-phenyl)-morpholin-4-yl]-ethanol (1.33 g; 4.0 mmol) in a mixture of THF (15 mL) and CH2Cl2 (15 mL) was added a tetrazole solution in CH3CN (17.6 mL; 0.45 mol/L; 7.9 mmol) at RT. The resulting mixture was stirred for 30 minutes and subsequently di-tert-butyl N,N-diisopropylphosphoramidite (2.00 ml; 6.3 mmol) was added and stirred overnight at RT. Subsequently, an aqueous hydrogen peroxide solution (1.80 ml; 300 g/1; 15.9 mmol) was added and the mixture stirred at RT for another 15 min. The reaction was quenched by the addition of an 5% aqueous NaHCO3 solution and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O) to afford phosphoric acid di-tert-butyl ester 2-[2-(4-octyloxy-phenyl)-morpholin-4-yl]-ethyl ester (0.71 g).

Workup

  1. stirringstirred overnight at RT
  2. stirringthe mixture stirred at RT for another 15 min
  3. customThe reaction was quenched by the addition of an 5% aqueous NaHCO3 solution
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (SiO2, Et2O)

Sources & evidence

ORD record
ord-0425bf11583a435fa7eeafa0d5ea8e00
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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