Hydrogen Peroxide → tert-Butyl 4-(2-hydroxyethyl)naphthalen-1-ylcarbamate

HRID 2069038Notes

Reaction equation

HRID 2069038 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:5][CH:4]=1)=[CH2:2].B1C2CCCC1CCC2.[OH-:30].[Na+].OO>C1COCC1.O>[OH:30][CH2:2][CH2:1][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 68313610tert-Butyl 4-vinylnaphthalen-1-ylcarbamate

Product 1

HCID 68313879tert-Butyl 4-(2-hydroxyethyl)naphthalen-1-ylcarbamateYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-vinylnaphthalen-1-ylcarbamate (31) (0.83 g, 3.08 mmol) in THF (10 mL) was added 9-BBN (0.5M in THF, 9.9 mL, 4.95 mmol) dropwise under nitrogen at 0° C. The mixture was warmed to RT and stirred for 16 hr. Water (1 mL), aqueous NaOH solution (3M, 10.0 mL, 30 mmol) and hydrogen peroxide (35% in water, 8.0 mL) were added. The reaction mixture was warmed to 50° C. and stirred for 2 hr and was then extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 10-60% ethyl acetate in isohexane, gradient elution) to afford the title compound (32) (0.763 g, 86%); m/z 288 (M+H)+, (ES+).

Workup

  1. temperatureThe reaction mixture was warmed to 50° C.
  2. stirringstirred for 2 hr
  3. extractionwas then extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography (SiO2, 10-60% ethyl acetate in isohexane, gradient elution)

Sources & evidence

ORD record
ord-84e8f4e18d3448bebabab9f732efd8a8
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

Loading…