Hydrogen Peroxide → HCID 25242003, compound

HRID 2099535Notes

Reaction equation

HRID 2099535 reaction equation
[BH4-].[Na+].CC1C2C(C)(C)C(C2)CC=1.[C:13]1([CH:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:20]2[CH2:24][CH:23]=[CH:22][CH2:21]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH:31]O.[OH-].[Na+]>O1CCCC1>[C:13]1([CH:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:20]2[CH2:24][CH2:23][C@H:22]([OH:31])[CH2:21]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 6654(+-)-alpha-PineneHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 11195696HCID 11195696, compound

Product 1

HCID 25242003HCID 25242003, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.235 mg) was suspended in tetrahydrofuran (2.0 mL) in an argon flow, and the suspension was cooled with ice. Optically active α-pinene (0.63 mL) and boron trifluoride-ether complex (0.25 mL) were added dropwise to the suspension, and the mixture was stirred for 12 hours. 1-Diphenylmethyl-3-pyrroline (0.24 g) was added to the reaction mixture, and the resultant mixture was allowed to react for 9 hours. Thereafter, 30% aqueous hydrogen peroxide (2 mL) and 6 mol/L aqueous sodium hydroxide (2 mL) were added dropwise to the reaction mixture. After 3 h, the reaction mixture was extracted with methylene chloride, and the formed organic layer was dried over sodium sulfate. The drying agent was removed through filtration, and the filtrate was concentrated under reduced pressure, to thereby yield crystalline residue. The residue was subjected to silica gel chromatography, to thereby give the target compound (0.200 g, yield 79%). HPLC analysis (through use of a Daicel Chiral Pack AD-RH) of the thus-obtained compound indicates that the compound has an optical purity of 72% ee.

Workup

  1. temperaturethe suspension was cooled with ice
  2. customto react for 9 hours
  3. waitAfter 3 h
  4. extractionthe reaction mixture was extracted with methylene chloride
  5. dry with materialthe formed organic layer was dried over sodium sulfate
  6. customThe drying agent was removed through filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3cd9dfd6b251447594367a28247b3341
Source dataset
uspto-grants-2009_08
Patent number
US07569599B2

Reaction notes

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