Hydrogen Peroxide → HCID 68234528, compound

HRID 2276755Notes

Reaction equation

HRID 2276755 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:27])([CH3:26])[CH2:9][N:10]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH2:25])=[CH:20][N:19]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.B.[OH-:29].[Na+].OO>[Cl-].[Na+].O.C(O)C.C1COCC1.C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:27])([CH3:26])[CH2:9][N:10]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][OH:29])=[CH:20][N:19]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 67453738HCID 67453738, compound

Product 1

HCID 68234528HCID 68234528, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 21873804Tetrahydrofuran ethanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
35 °C

Procedure

To a 20 dram vial was added tert-butyl 2-(4-fluorophenyl)-2-methylpropyl(5-vinylpyridin-2-yl)carbamate (2.4 g, 6.4 mmol, 1.0 equiv) and THF (20 mL). Borane (7.7 mL, 7.7 mmol, 4.0 equiv) was added slowly, and the reaction was heated to 35° C. and stirred for 45 min. The reaction was then cooled to 0° C. followed by the addition of a 50% ethanol/THF mixture (25 mL), 2N sodium hydroxide (13 mL, 25.8 mmol, 4.0 equiv), and 30% hydrogen peroxide (15 mL). The reaction was stirred for 1 h, diluted with brine (10 mL), and extracted with ethyl acetate (20 mL). The organic layer was dried over Na2SO4, filtered, concentrated, and then purified by reverse phase column chromatography to give 414 mg (17%) of tert-butyl 2-(4-fluorophenyl)-2-methylpropyl(5-(2-hydroxyethyl)pyridin-2-yl)carbamate.

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. stirringThe reaction was stirred for 1 h
  3. extractionextracted with ethyl acetate (20 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by reverse phase column chromatography

Sources & evidence

ORD record
ord-8311acfbc86648568229328d30cffee1
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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