m-Chloroperbenzoic acid → [3-(4-Bromophenyl)-4,5-dihydroisoxazol-5-yl]methyl di-tert-butyl phosphate

HRID 747243Notes

Reaction equation

HRID 747243 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][OH:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.[C:15]([O:19][P:20](N(CC)CC)[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:18])([CH3:17])[CH3:16].N1C=NN=N1.ClC1C=CC=C(C(OO)=[O:44])C=1.S(=O)(O)[O-].[Na+]>ClCCl>[P:20]([O:19][C:15]([CH3:16])([CH3:17])[CH3:18])([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])([O:14][CH2:13][CH:11]1[O:10][N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH2:12]1)=[O:44]

Participants

7

Reactant 5

HCID 70297m-Chloroperbenzoic acidHCID 4251849Di-tert-butyl diethylphosphoramiditeHCID 15888252[3-(4-Bromophenyl)-4,5-dihydro-1,2-oxazol-5-yl]methanolHCID 23665763Sodium BisulfiteHCID 178418441HCID 178418441, compound

Product 1

HCID 68597275[3-(4-Bromophenyl)-4,5-dihydroisoxazol-5-yl]methyl di-tert-butyl phosphate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[3-(4-Bromophenyl)-4,5-dihydroisoxazol-5-yl]methanol (2.5 g, 9.8 mmol) was dissolved in dichloromethane (100 ml). To this solution, di-tert-butyl-N,N-diethylphosphoroamidite (3.3 ml, 11.7 mmol) and 1H-tetrazole (1.2 g, 17.6 mmol) were added sequentially. After 1.5 h stirring at room temperature, the solution was cooled to 0° C. and m-chloroperbenzoic acid (70%; 3.6 g, 14.7 mmol) was added. After 1.5 h the reaction was warmed to room temperature; a sodium bisulfite solution was added and the mixture stirred about 5 min. After diluting with dichloromethane, the aqueous layer was extracted with dichloromethane (2×), and the combined organics were washed with saturated sodium bicarbonate solution, brine, and dried over magnesium sulfate. The crude residue was purified by chromatography on silica gel using 0-5% methanol in dichloromethane as the eluent, resuliting in 4.1 g of the desired product.

Workup

  1. temperaturethe solution was cooled to 0° C.
  2. temperatureAfter 1.5 h the reaction was warmed to room temperature
  3. stirringthe mixture stirred about 5 min
  4. extractionthe aqueous layer was extracted with dichloromethane (2×)
  5. washthe combined organics were washed with saturated sodium bicarbonate solution, brine
  6. dry with materialdried over magnesium sulfate
  7. customThe crude residue was purified by chromatography on silica gel using 0-5% methanol in dichloromethane as the eluent

Sources & evidence

ORD record
ord-79413ccb140647c88783620536dbe508
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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