Hydrogen Peroxide → HCID 18009421, compound

HRID 987603Notes

Reaction equation

HRID 987603 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH2:8][NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[O:11])[CH2:4][CH2:3]1.B1C2CCCC1CCC2.[OH-:35].[Na+].OO>C1COCC1.C(Cl)Cl>[OH:35][CH2:1][CH:2]1[CH2:7][CH2:6][C:5]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([CH2:8][NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[O:11])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 18009445HCID 18009445, compound

Product 1

HCID 18009421HCID 18009421, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methylidene-4-phenyl-4-(3-(2-methoxyphenyl)-3-oxo-2-azaprop-1-yl)cyclohexane (Example 165, 117 mg, 0.35 mmol) was added 9-BBN (7 mL, 0.5 N, 3.5 mmol) in THF. The reaction mixture was stirred at rt for 1 h, and then heated to 45° C. for 3 h. To the solution was then added NaOH (3 mL, 10%) and H2O2 (4 mL, 30%) and the mixture was heated at 45° C. for 14 h. The reaction mixture was poured into CH2Cl2 and washed with 2N HCl and dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica, EtOAc/hexane, 2:1) to give the title compound as a 2:1 mixture of two diastereomers.

Workup

  1. temperatureheated to 45° C. for 3 h
  2. washwashed with 2N HCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica, EtOAc/hexane, 2:1)

Sources & evidence

ORD record
ord-ad187d22499b4418b29558fa89eab324
Source dataset
uspto-grants-2003_10
Patent number
US06632836B1

Reaction notes

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