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

HRID 1507269노트

반응식

HRID 1507269 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-219c7eb3f2b644b28dee9a669c6e847d
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221796B2

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