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

HRID 1011601
ノート
印刷プレビュー

反応式

HRID 1011601 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-82b9dc411bcc47baac316312160e4b01
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07977368B2

反応ノート

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