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

HRID 2223426ノート

反応式

HRID 2223426 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11513808Pd/C(en)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e5a1460c87904dc384b3dcf75db7486b
出典データセット
uspto-grants-2008_05
特許番号
US07375136B2

反応ノート

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