Imidazole → 4-{[tert-Butyl(dimethyl)silyl]oxy}-1-(1-methyl-1H-imidazol-2-yl)piperidine

HRID 2095744ノート

反応式

HRID 2095744 の反応式
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[N:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CN=C1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Si:14]([O:13][CH:10]1[CH2:9][CH2:8][N:7]([C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=2)[CH2:12][CH2:11]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

参加物

6

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 621338431-(1-Methyl-1H-imidazol-2-yl)piperidin-4-ol

生成物 1

HCID 670039784-{[tert-Butyl(dimethyl)silyl]oxy}-1-(1-methyl-1H-imidazol-2-yl)piperidine

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 1-(1-Methyl-1H-imidazol-2-yl)piperidin-4-ol (0.200 g, 1.10 mmol), tert-Butyldimethylsilyl chloride (0.333 g, 2.21 mmol), 4-Dimethylaminopyridine (30 mg, 0.2 mmol), 1H-Imidazole (225 mg, 3.31 mmol) and DCM (6.0 mL, 94 mmol) was stirred at ambient temperature for 1 h. The reaction mixture was diluted with DCM to ≈60 mL, washed with sat. NaHCO3 solution, water, and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel [Isco Combiflash, 2.5 g loading column/12 g column, eluting with DCM→5% MeOH in DCM]. Fractions containing the title compound were combined and dried in vacuo overnight, giving the title compound as yellow oil. 1H NMR (400 MHz, CDCl3): δ=6.77 (d, J=1.2 Hz, 1H), 6.65 (d, J=1.4 Hz, 1H), 3.85 (tt, J=8.0, 3.8 Hz, 1H), 3.47 (s, 3H), 3.28-3.21 (m, 2H), 2.91 (br ddd, J=12.0, 9.0, 3.0 Hz, 2H), 1.92-1.84 (m, 2H), 1.73-1.64 (m, 2H), 0.90 (s, 9H), 0.07 (s, 6H). MS (ES+): m/z=296.29 (100) [MH+]. HPLC: tR=3.22 min (verypolar—5 min, ZQ3). UV: λmax≈240 nm.

後処理

  1. washwashed with sat. NaHCO3 solution, water, and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel [Isco Combiflash, 2.5 g loading column/12 g column, eluting with DCM→5% MeOH in DCM]
  6. additionFractions containing the title compound
  7. customdried in vacuo overnight

出典と根拠

ORDレコード
ord-4a1daee541db46e8b656d3b531b2c4cc
出典データセット
uspto-grants-2013_05
特許番号
US08445510B2

反応ノート

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