2-Methyltetrahydrofuran → Tert-butyl 4-[4-iodo-1-(2-pyrrolidin-1-ylethyl)imidazol-2-yl]piperidine-1-carboxylate

HRID 2088936

반응식

HRID 2088936 반응식
[I:1][C:2]1[N:3]=[C:4]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[N:5]([CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]=1I.CC1CCCO1.C([Mg]Cl)(C)C.O1CCCC1.[Cl-].[NH4+]>>[I:1][C:2]1[N:3]=[C:4]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[N:5]([CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:6]=1

참가 물질

6

반응물 5

HCID 73012-MethyltetrahydrofuranHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 67112102Tert-butyl 4-[4,5-diiodo-1-(2-pyrrolidin-1-ylethyl)imidazol-2-yl]piperidine-1-carboxylateHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 67112018Tert-butyl 4-[4-iodo-1-(2-pyrrolidin-1-ylethyl)imidazol-2-yl]piperidine-1-carboxylate수율 98%

반응 조건

온도
0 °C

실험 절차

Combine tert-butyl 4-(4,5-diiodo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate (51.00 g, 84.96 mmol) and 2-methyltetrahydrofuran (357 mL). Cool the reaction mixture to 0° C. Add 2 M isopropylmagnesium chloride in tetrahydrofuran (55.22 mL, 1.3 eq) dropwise over 45 minutes, maintaining the temperature below 5° C. Add saturated aqueous ammonium chloride. Separate the layers. Wash the aqueous phase with methyl tert-butyl ether. Wash the organics with aqueous saturated sodium chloride. Dry the organics over anhydrous magnesium sulfate, decolor with charcoal, filter, and concentrate in vacuo to give tert-butyl 4-(4-iodo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate as a yellow solid (39.50 g, 98%). MS (ES) m/z=475 [M]+.

후처리

  1. temperaturemaintaining the temperature below 5° C
  2. customSeparate the layers
  3. washWash the aqueous phase with methyl tert-butyl ether
  4. washWash the organics with aqueous saturated sodium chloride
  5. dry with materialDry the organics over anhydrous magnesium sulfate, decolor with charcoal
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

출처 및 근거

ORD 기록
ord-a90feec47fa34ccaa44c7d060d23aae6
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436002B2

연결된 노트

불러오는 중…