Hydrogen Peroxide → HCID 58380936, compound

HRID 45211Notes

Reaction equation

HRID 45211 reaction equation
[NH2:1][CH:2]([C:5]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:9][CH:8]=[CH:7][CH2:6]1)[CH2:3][CH3:4].B.[OH:18]O.[OH-].[Na+]>C1COCC1.O>[NH2:1][CH:2]([C:5]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH:8]([OH:18])[CH2:9]1)[CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 58380954HCID 58380954, compound

Product 1

HCID 58380936HCID 58380936, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(1-aminopropyl)-1-(4-fluorophenyl)cyclopent-3-ene (118, 348 mg, 1.6 mmol) was dissolved in THF at 0° C. under argon. Borane (1.75 mL, 1.75 mmol, 1M in THF) was added dropwise over 10 minutes. The reaction mixture was allowed to warm to room temperature before stirring overnight. After cooling to 0° C., water was added (4 mL), followed by hydrogen peroxide (0.61 mL, 30% solution in water) and sodium hydroxide solution (1.75 mL, 1M aqueous solution). After stirring for 5 minutes the mixture was extracted with ethyl acetate, dried over sodium sulphate and evaporated to give 458 mg of desired product, which was stirred for 15 minutes with dilute hydrochloric acid (10 mL, 2M aqueous solution). Evaporation, followed by freeze drying gave 514 mg of the desired product as mixture of four stereoisomers as a colourless hydrochloride salt. Rt=1.83, 1.99, 2.36, 2.86 min (Method 2). Detected mass: 203.1 (M—NH3—H2O+H+).

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringAfter stirring for 5 minutes the mixture
  3. extractionwas extracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-5187aabffc5d4fc89f38a9bb8e51c585
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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