Hydrogen Peroxide → HCID 10635973, compound

HRID 1697886Notes

Reaction equation

HRID 1697886 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][C@H:10]1[CH:12]=[CH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].B1C2CCCC1CCC2.C([O-])(=[O:30])C.[Na+].OO>C1COCC1.CCCCCC.CCOC(C)=O>[OH2:5].[C:1]([O:5][C:6]([NH:8][C@:9]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][C@H:10]1[CH2:12][CH2:13][OH:30])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 517045Sodium AcetateHCID 10658673Ethyl (1R,2S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenylcyclopropanecarboxylate

Product 2

HCID 962WaterHCID 10635973HCID 10635973, compoundYield 140.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of (1R,2S)-ethyl 1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate (15.3 g, 59.9 mmol) in THF (100 ml) was added 9-BBN (180 ml, 90 mmol) dropwise at 0° C. The formed solution was stirred at room temperature for 2 hr. The final solution was cooled back to 0° C. while 3 M aqueous solution of sodium acetate (180 ml, 540 mmol) was added. To this well stirred mixture, Hydrogen peroxide (89 ml, 30%, 869 mmol) was added dropwise (Caution should be exercised since the addition was exothermic). The formed warm two layer mixture was stirred overnight. The upper organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated. The residue was purified by silica gel column, eluted with 4:1, 3:1, 2:1, then 3:2 Hexane-EtOAc to afford the desired product (1R,2S)-ethyl 1-(tert-butoxycarbonylamino)-2-(2-hydroxyethyl)cyclopropanecarboxylate (11.50 g, 42.1 mmol, 70.2% yield) as a viscous oil, which solidified upon standing on the bench. 1H NMR (CDCl3) δ 1.18-1.21 (m, 1H), 1.25 (t, J=7 Hz, 3H), 1.35-1.40 (m, 1H), 1.44 (s, 9H), 1.61-1.65 (m, 1H), 1.70-1.75 (m, 1H), 1.91-1.98 (m, 1H), 3.61-3.65 (m, 1H), 3.71-3.75 (m, 1H), 4.10-4.21 (m, 2H), 5.17 (b, 1H).

Workup

  1. additionwas added
  2. additionwas added dropwise (Caution
  3. additionshould be exercised since the addition
  4. temperatureThe formed warm two layer mixture
  5. stirringwas stirred overnight
  6. customThe upper organic layer was separated
  7. extractionthe aqueous layer was extracted with EtOAc
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified by silica gel column
  13. washeluted with 4:1, 3:1, 2:1

Sources & evidence

ORD record
ord-08695506dec94afb8a5cd04ff0cd9d4a
Source dataset
uspto-grants-2012_04
Patent number
US08163921B2

Reaction notes

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