Hydrogen Peroxide → HCID 67951398, compound

HRID 1054535Notes

Reaction equation

HRID 1054535 reaction equation
[O:1]1CCCC1.[CH2:6]([O:13][C:14](=[O:27])[NH:15][C@H:16]1[C@H:23]2[C@H:19]([O:20][C:21]([CH3:25])([CH3:24])[O:22]2)[C:18](=[CH2:26])[CH2:17]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].OO>O>[CH2:6]([O:13][C:14](=[O:27])[NH:15][C@H:16]1[C@H:23]2[C@H:19]([O:20][C:21]([CH3:24])([CH3:25])[O:22]2)[C@H:18]([CH2:26][OH:1])[CH2:17]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 67951331HCID 67951331, compound

Product 1

HCID 67951398HCID 67951398, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Borane-THF complex in tetrahydrofuran (1M, 0.99 mL, 0.99 mmol) was added to a 0° C. solution of benzyl((3aS,4R,6aR)-2,2-dimethyl-6-methylenetetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate (0.150 g, 0.494 mmol) in tetrahydrofuran (10 mL, 0.1 mol). Some bubbling initially observed, the mixture stirred at room temperature for 1 hour. The reaction was quenched via the addition of aqueous sodium hydroxide (4M, 1.24 mL, 0.00494 mol) and hydrogen peroxide 35% (35%, 0.425 ml, 4.94 mmol) were added and reaction stirred at room temperature for 2.5 hours. Water (5 ml) added to the reaction and the aqueous was extracted with ether (3×50 mls). The combined organics were dried with MgSO4 and purified by FC (Hex/EtOAc 1:1) to yield benzyl((3aS,4R,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate (0.070 g, 44%) as a thick colorless oil: MS (ESI+) for C17H23NO5 m/z 344.2 [M+Na]+; MS (ESI−) for C17H23NO5 m/z 320.3 [M−H]−;

Workup

  1. additionwere added
  2. customreaction
  3. stirringstirred at room temperature for 2.5 hours
  4. extractionthe aqueous was extracted with ether (3×50 mls)
  5. dry with materialThe combined organics were dried with MgSO4
  6. custompurified by FC (Hex/EtOAc 1:1)

Sources & evidence

ORD record
ord-e307763db14a4f339cd4711e6764c3ca
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

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