Hydrogen Peroxide → HCID 58027642, compound

HRID 882437Notes

Reaction equation

HRID 882437 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C:15](=[CH2:26])[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:27].[Na+].OO>C1COCC1>[CH:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]([CH2:26][OH:27])[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 58027576HCID 58027576, compound

Product 1

HCID 58027642HCID 58027642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl 3-(3-(cyclohexylmethoxy)phenyl)but-3-enylcarbamate (90) (0.32 g, 0.89 mmol) in THF (10 ml) was added BH3 (1 M in THF, 2.4 ml, 2.4 mmol) at room temperature. After stirring for 4 hr, aqueous NaOH (1 M, 6.0 ml, 6.0 mmol) was added and the mixture was stirred at 60° C. for 2.5 hrs and room temperature for 18 hr. The mixture was added H2O2 (6 ml, 30%) and stirred at 50° C. for 2 hr. The reaction mixture was extracted with ethyle acetate (2×50 ml). Ethyle acetate part was washed with brine (50 ml), dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography (30 to 75% EtOAc-hexanes gradient) gave tert-butyl 3-(3-(cyclohexylmethoxy)phenyl)-4-hydroxybutylcarbamate (92) as a colorless oil. Yield (0.2 g, 60%): 1H NMR (400 MHz, MeOD) δ 7.17 (t, J=8.0 Hz, 1H), 6.73-6.78 (m, 3H), 3.74 (d, J=6.4 Hz, 2H), 3.58-3.68 (m, 2H), 2.91 (t, J=7.8 Hz, 2H), 2.66-2.76 (m, 1H), 1.85-2.00 (m, 3H), 1.67-1.78 (m, 5H), 1.39 (s, 9H), 1.20-1.35 (m, 3H), 1.01-1.14 (m, 2H).

Workup

  1. stirringthe mixture was stirred at 60° C. for 2.5 hrs and room temperature for 18 hr
  2. stirringstirred at 50° C. for 2 hr
  3. extractionThe reaction mixture was extracted with ethyle acetate (2×50 ml)
  4. washEthyle acetate part was washed with brine (50 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (30 to 75% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-33d08b70b6b14987b9e71ae33347df12
Source dataset
uspto-grants-2015_03
Patent number
US08993807B2

Reaction notes

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