Hydrogen Peroxide → HCID 58380846, compound

HRID 1948157Notes

Reaction equation

HRID 1948157 reaction equation
[NH2:1][CH:2]([C:5]1([CH2:10][CH2:11][CH3:12])[CH2:9][CH:8]=[CH:7][CH2:6]1)[CH2:3][CH3:4].B.[OH:14]O.[OH-].[Na+]>C1COCC1.O>[NH2:1][CH:2]([C:5]1([CH2:10][CH2:11][CH3:12])[CH2:9][CH2:8][CH:7]([OH:14])[CH2:6]1)[CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 58380836HCID 58380836, compound

Product 1

HCID 58380846HCID 58380846, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(1-aminopropyl)-1-propylcyclopent-3-ene (63, 1.4 g, 8.25 mmol) was dissolved in THF (15 mL) at 0° C. under argon. Borane (9.1 mL, 9.07 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 (5.8 mL, 30% solution in water) and sodium hydroxide solution (9.1 mL, 1M aqueous solution). After stirring for 5 minutes the mixture was extracted with ethyl acetate, dried over sodium sulphate and evaporated to give 1.54 g of desired product as a mixture of isomers. Rt=0.81, 0.84, 0.88 min (Method M). Detected mass: 186.2 (M+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-ca2e15452a994136acfbe979b13c21b5
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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