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Ammonium Chloride → (S)-t-Butyl 2-(4-((tert-butyldiphenylsilyl)oxy)but-2-ynoyl)pyrrolidine-1-carboxylate

HRID 710033
ノート
印刷プレビュー

反応式

HRID 710033 の反応式
[Li]CCCC.[C:6]([Si:10]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:11][CH2:12][C:13]#[CH:14])([CH3:9])([CH3:8])[CH3:7].CON(C)[C:30]([C@@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:31].[NH4+].[Cl-]>C1COCC1>[Si:10]([O:11][CH2:12][C:13]#[C:14][C:30]([C@@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:31])([C:6]([CH3:9])([CH3:7])[CH3:8])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 610226Silane, (1,1-dimethylethyl)diphenyl(2-propynyloxy)-HCID 6882981,1-Dimethylethyl (2S)-2-[(methoxymethylamino)carbonyl]-1-pyrrolidinecarboxylateHCID 178418339Butyllithium

生成物 1

HCID 86706745(S)-t-Butyl 2-(4-((tert-butyldiphenylsilyl)oxy)but-2-ynoyl)pyrrolidine-1-carboxylate収率 56.2%

試薬・触媒・溶媒

1
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In an argon atmosphere, n-BuLi (10.3 mL, 2.64 N hexane solution) was added dropwise to a solution of t-butyldiphenyl(prop-2-yn-1-yloxy)silane (8.576 g) in THF (200 mL) at −78° C. over 10 minutes, and after stirring at room temperature for 50 minutes, the reaction mixture was added dropwise to a solution of (S)-t-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (5.01 g) in THF (200 mL) through a cannula and temperature was raised to room temperature over an hour. The reaction mixture was added to a saturated aqueous solution of NH4Cl (500 mL) and, after extraction with AcOEt, the organic layer was dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by neutral silica gel chromatography (AcOEt/hexane) to give the titled compound (5.36 g, colorless oil.)

後処理

  1. temperaturewas raised to room temperature over an hour
  2. extractionafter extraction with AcOEt
  3. dry with materialthe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product, which
  7. customwas further purified by neutral silica gel chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-2a5341d7992c42738b741facc0a034e5
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181229B2

反応ノート

読み込み中…

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