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

HRID 2088936

反応式

HRID 2088936 の反応式
[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

参加物

6

反応物 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、化合物

生成物 1

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

反応条件

温度
0 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-a90feec47fa34ccaa44c7d060d23aae6
出典データセット
uspto-grants-2013_05
特許番号
US08436002B2

関連ノート

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