(S)-2-((3-Nitrophenoxy)methyl)oxirane → 3-{[(2S)-Oxiran-2-yl]methoxy}aniline

HRID 2223426Notes

Reaction equation

HRID 2223426 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([O:10][CH2:11][C@H:12]2[O:14][CH2:13]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>C1COCC1.[Pd].NCCN>[NH2:1][C:4]1[CH:5]=[C:6]([O:10][CH2:11][C@H:12]2[O:14][CH2:13]2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 7036817(S)-2-((3-Nitrophenoxy)methyl)oxirane

Product 1

HCID 450910383-{[(2S)-Oxiran-2-yl]methoxy}aniline

Reagents, catalysts & solvents 2

HCID 11513808Pd/C(en)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Compound 16a-S (0.5 g, 2.6 mmol) and % 5 Pd/C(en) (10% of the weight of starting material) in 5 ml anhydrous THF was hydrogenated at ambient pressure and temperature for 3-5 hours. The reaction mixture was filtered by using a membrane filter (13, 0.22 μm), and the filtrate was concentrated in vacuo. The resulting compound is a crude mixture of nitro group reduction and epoxide ring opening. Isolation of the desired compound was difficult because of the lability of the components of the mixture on silica gel. The product ratio of the NO2 reduction and ring opening (80:20) was determined on the basis of the integration ratio of the epoxide-ring protons from nitro group reduction and the methyl proton of the ring opened compound (98% total yield for the mixture).

Workup

  1. filtrationThe reaction mixture was filtered
  2. filtrationfilter (13, 0.22 μm)
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionmixture of nitro group reduction and epoxide ring opening
  5. customtotal yield for the mixture)

Sources & evidence

ORD record
ord-e5a1460c87904dc384b3dcf75db7486b
Source dataset
uspto-grants-2008_05
Patent number
US07375136B2

Reaction notes

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