Hydrogen Peroxide → HCID 57188213, compound

HRID 850287Notes

Reaction equation

HRID 850287 reaction equation
[CH2:1]([C@H:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7](=[O:16])[C@H:6]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C@H:5]1[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH:2]=[CH2:3].C(O)(=O)[C@H]([C@@H](C(O)=O)O)[OH:35].[OH-].[Na+].OO>O1CCCC1.C(OCC)(=O)C.O>[CH2:9]([N:8]1[C@H:4]([CH2:1][CH2:2][CH2:3][OH:35])[C@H:5]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28])[C@@H:6]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])[C:7]1=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 439655D-Tartaric acidHCID 10412681HCID 10412681, compound

Product 1

HCID 57188213HCID 57188213, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

100 g of (3R*,4S*,5R*)-5-allyl-1-benzyl-3,4-bis(tert-butyidimethylsilyloxy)-2-pyrrolidinone which had been prepared according to the procedure described in J. Org. Chem. 60, 103-108 (1995) by using D-tartaric acid as the starting material was added to 670 ml of tetrahydrofuran, and cooled with ice. Then, 87.1 ml of a 1.0M solution of borane-tetrahydrofuran complex in tetrahydrofuran was added thereto. After this mixture was stirred at room temperature for 1 hour, 7 ml of water was added dropwise thereto, and 33.4 ml of a 5N aqueous solution of sodium hydroxide was added at a time. Then, 33.4 ml of a 30% aqueous solution of hydrogen peroxide was added thereto at such a rate as to give a reaction temperature of 30-50° C., followed by stirring overnight. Thereafter, water and ethyl acetate were added to the reaction mixture so as to extract the product in an organic layer. After this organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (using chloroform as the eluent) to obtain 33.4 g of (3R*,4S*,5R*)-1-benzyl-3,4-bis(tert-butyidimethylsilyloxy)-5-(3-hydroxypropyl)-2-pyrrolidinone.

Workup

  1. temperaturecooled with ice
  2. customat such a rate as to give a reaction temperature of 30-50° C.
  3. stirringby stirring overnight
  4. extractionto extract the product in an organic layer
  5. dry with materialAfter this organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-9d513e8e9c3c4025a9c1ca99db0cdf0d
Source dataset
uspto-grants-2000_01
Patent number
US06017911

Reaction notes

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