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Imidazole → (2S,3R)-tert-Butyl 3-(tert-butyldimethylsilyloxy)-2-cyclopropyl-5-oxopyrrolidine-1-carboxylate

HRID 1011601
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HRID 1011601 반응식
[CH:1]1([C@H:4]2[C@H:8]([OH:9])[CH2:7][C:6](=[O:10])[N:5]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:2]1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].N1C=CN=C1>CN(C=O)C>[Si:22]([O:9][C@@H:8]1[CH2:7][C:6](=[O:10])[N:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:4]1[CH:1]1[CH2:2][CH2:3]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23]
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참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57659767(2S,3R)-tert-Butyl 2-cyclopropyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate

생성물 1

HCID 67313766(2S,3R)-tert-Butyl 3-(tert-butyldimethylsilyloxy)-2-cyclopropyl-5-oxopyrrolidine-1-carboxylate수율 90.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

(2S,3R)-tert-Butyl 2-cyclopropyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate (16) (1.34 g, 5.55 mmol) was placed in a flame-dried flask under nitrogen. DMF (12 mL) was added and the mixture stirred until dissolved. tert-butylchlorodimethylsilane (1.06 g, 7.02 mmol) and imidazole (0.558 g, 8.19 mmol) were added and the reaction stirred for 16 hr at rt. DMF was removed in vacuo and EtOAc (100 mL) was added and the organics were washed with sat. NaHCO3 (100 mL), brine (100 mL), dried with sodium sulfate, and concentrated in vacuo. The resulting crude product was purified via column chromatography using EtOAc/hexane gradients to yield (2S,3R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-cyclopropyl-5-oxopyrrolidine-1-carboxylate (17) (1.78 g, 90%) as a white solid.

후처리

  1. dissolutionuntil dissolved
  2. stirringthe reaction stirred for 16 hr at rt
  3. customDMF was removed in vacuo and EtOAc (100 mL)
  4. additionwas added
  5. washthe organics were washed with sat. NaHCO3 (100 mL), brine (100 mL)
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude product was purified via column chromatography

출처 및 근거

ORD 기록
ord-82b9dc411bcc47baac316312160e4b01
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07977368B2

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