Hydrogen Peroxide → Ammonium Hydroxide

HRID 1824100Notes

Reaction equation

HRID 1824100 reaction equation
[CH2:1]1[C:10]2[C:5](=CC=C[CH:9]=2)[CH:4]=[CH:3][CH2:2]1.F[C:12](F)(F)[C:13](=[O:15])[CH3:14].OO.C(#[N:22])C>C(=O)([O-])[O-].[K+].[K+]>[NH4+:22].[OH-:15].[NH2:22][C@@H:12]1[C:5]2[C:10](=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:9][CH2:14][C@H:13]1[OH:15]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 6342AcetonitrileHCID 9871Methyl trifluoromethyl ketoneHCID 99381,2-Dihydronaphthalene

Product 2

HCID 14923Ammonium HydroxideYield 0.5%HCID 13125680(1R,2R)-1-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 1,2-dihydronaphthalene (5.12 g) and trifluoroacetone (1.34 g) in acetonitrile (60 ml) and aqueous potassium carbonate (1.5M in 0.4 mM EDTA, 60 ml) was added H2O2 (30%, 18.2 ml) at 0° C. Upon stirring at 0° C. for 4 hours, the rxn mixture was extracted with Et2O, washed with aqueous Na2S2O3 (1M) and brine, dried (MgSO4), filtered and concentrated. The epoxide was used without purification. A mixture of 1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene and ammonium hydroxide was stirred at 40° C. for 3 days. The excess solvent was removed in vacuo. Flash chromatography (Silica gel, 1:20 MeOH:CH2Cl2, 0.5% NH4OH) gave the title compound. HRMS (FAB) calcd for C10H13NO+H 164.1075, found 164.1075.

Workup

  1. extractionthe rxn mixture was extracted with Et2O
  2. washwashed with aqueous Na2S2O3 (1M) and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe epoxide was used without purification
  7. additionA mixture of 1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene and ammonium hydroxide
  8. stirringwas stirred at 40° C. for 3 days
  9. customThe excess solvent was removed in vacuo

Sources & evidence

ORD record
ord-3b039b4ed5a842a291690b0a2994b027
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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