tert-Butyl hydroperoxide → HCID 67032466, compound

HRID 920593Notes

Reaction equation

HRID 920593 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[O:17][CH2:16][CH2:15][N:14]([CH2:18][CH2:19][OH:20])[CH2:13]2)=[CH:8][CH:7]=1.N1C=NN=N1.C(N(C(C)C)[P:35]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])(C)C.C([O:53]O)(C)(C)C.CCCCCCCCC>C1COCC1.C(Cl)Cl.CC#N>[Cl:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:2]([Cl:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[O:17][CH2:16][CH2:15][N:14]([CH2:18][CH2:19][O:20][P:35](=[O:53])([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])[O:41][C:42]([CH3:43])([CH3:44])[CH3:45])[CH2:13]2)=[CH:10][CH:11]=1

Participants

9

Reactant 5

HCID 6410tert-Butyl hydroperoxideHCID 8141NonaneHCID 853005Di-tert-butyl N,N-DiisopropylphosphoramiditeHCID 67033108HCID 67033108, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 67032466HCID 67032466, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of 2-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-ethanol (0.74 g; 1.94 mmol) in a mixture of THF (10 mL) and CH2Cl2 (10 mL) was added a tetrazole solution in CH3CN ((8.60 ml; 0.45 mol/1; 3.87 mmol) at RT. The resulting mixture was stirred for 30 minutes and subsequently di-tert-butyl N,N-diisopropylphosphoramidite (0.98 ml; 3.10 mmol) was added and stirred overnight at RT. Subsequently, the mixture was cooled to 4° C., and a solution of tert-butyl hydroperoxide in nonane (0.31 ml; ˜5.5 mol/L, 2.90 mmol) was added. Thereafter the mixture was stirred at RT for another 30 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, EtOAc) to afford phosphoric acid di-tert-butyl ester 2-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-ethyl ester (0.66 g).

Workup

  1. stirringstirred overnight at RT
  2. stirringThereafter the mixture was stirred at RT for another 30 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, EtOAc)

Sources & evidence

ORD record
ord-bcfc32790f7046ca8869d4c75b98a37f
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

Loading…