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

HRID 2223426노트

반응식

HRID 2223426 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 11513808Pd/C(en)촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e5a1460c87904dc384b3dcf75db7486b
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375136B2

반응 노트

불러오는 중…