Tetrabutylammonium Fluoride → Tert-butyl 4-hydroxy-4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate

HRID 747005ノート

反応式

HRID 747005 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH:19][C:20]1([C:33]#[C:34][CH2:35][O:36][Si](C)(C)C)[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1>O1CCCC1>[OH:19][C:20]1([C:33]#[C:34][CH2:35][OH:36])[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:22][CH2:21]1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 219551731,1-Dimethylethyl 4-hydroxy-4-(3-trimethylsilyloxypropynyl)-1-piperidinecarboxylate

生成物 1

HCID 21955143Tert-butyl 4-hydroxy-4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate収率 88%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Tetrabutylammonium fluoride (1M in tetrahydrofuran, 80 ml, 80 mmol) was added to a solution of 1,1-dimethylethyl 4-hydroxy-4-(3-trimethylsilyloxypropynyl)-1-piperidinecarboxylate (from step (i) above; 24.4 g, 75 mmol) in tetrahydrofuran (300 ml) and the mixture was stirred at room temperature for 18 hours. The solvent was evaporated under reduced pressure and water (200 ml) was added. The mixture was extracted with ethyl acetate (2×200 ml) and the combined organic fractions were washed with water (2×200 ml) and brine (200 ml), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as an orange oil (16.8 g, 88%).

後処理

  1. customThe solvent was evaporated under reduced pressure and water (200 ml)
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate (2×200 ml)
  4. washthe combined organic fractions were washed with water (2×200 ml) and brine (200 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-ecdc51dc4d87408d952d3f4cf6833f6a
出典データセット
uspto-grants-2008_07
特許番号
US07393858B2

反応ノート

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