Imidazole → (S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-one

HRID 1507269ノート

反応式

HRID 1507269 の反応式
N1C=CN=C1.[CH3:6][C:7]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])[CH3:8].[OH:14][C@H:15]1[CH2:19][CH2:18][NH:17][C:16]1=[O:20]>CN(C)C1C=CN=CC=1.C(Cl)Cl.O>[Si:10]([O:14][C@H:15]1[CH2:19][CH2:18][NH:17][C:16]1=[O:20])([C:7]([CH3:9])([CH3:8])[CH3:6])([CH3:12])[CH3:11]

参加物

7

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11029774(3S)-3-hydroxypyrrolidin-2-one

生成物 1

HCID 10584804(S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-one収率 97.6%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

4-Dimethylaminopyridine (0.199 g, 1.63 mmol), imidazole (6.73 g, 99 mmol) and TBDMS-Cl (20.6 ml, 59.3 mmol) was added to a stirred solution of (S)-3-hydroxypyrrolidin-2-one (5.0 g, 49.5 mmol) in DCM (198 ml) at RT. The reaction mixture was stirred for 24 h and then diluted with water. The mixture was extracted with DCM. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified using silica gel column chromatography (50-80% EtOAc/hexanes) to afford (S)-3-((tert-butyldimethylsilyl)oxy)pyrrolidin-2-one (10.4 g, 97% yield) as a white solid: 1H NMR (500 MHz, chloroform-d) δ 6.15 (br. s., 1H), 4.28 (t, J=7.6 Hz, 1H), 3.40 (dddd, J=9.7, 8.5, 3.1, 1.2 Hz, 1H), 3.28 (dt, J=9.6, 7.4 Hz, 1H), 2.39 (dtd, J=12.7, 7.3, 3.1 Hz, 1H), 2.10-2.02 (m, 1H), 0.97-0.92 (m, 9H), 0.20-0.14 (m, 6H).

後処理

  1. extractionThe mixture was extracted with DCM
  2. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified

出典と根拠

ORDレコード
ord-219c7eb3f2b644b28dee9a669c6e847d
出典データセット
uspto-grants-2015_12
特許番号
US09221796B2

反応ノート

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