Tetrabutylammonium Fluoride → Tert-butyl 4-(4-ethynylphenyl)piperidine-1-carboxylate

HRID 1487941ノート

反応式

HRID 1487941 の反応式
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[C:6]([C:7]1[CH:8]=[CH:9][C:10]([CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[CH:11][CH:12]=1)#[CH:5]

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 59805220Tert-butyl 4-(4-((trimethylsilyl)ethynyl)phenyl)piperidine-1-carboxylate2 回

生成物 1

HCID 59805226Tert-butyl 4-(4-ethynylphenyl)piperidine-1-carboxylate収率 93.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Into a 50-mL round-bottom flask, was placed a solution of tert-butyl 4-(4-((trimethylsilyl)ethynyl)phenyl)piperidine-1-carboxylate (compound 76.2, 1.34 g, 3.75 mmol) in tetrahydrofuran (20 mL). Tetrabutylammonium fluoride (1.95 g, 7.47 mmol) was added and the resulting solution was stirred for 10 min at room temperature. The mixture was diluted with water (30 mL) and extracted with EtOAc (3×20 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated under reduced pressure to yield the title compound as a brown oil (1.0 g, crude).

後処理

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-cdaf1e369a05411ab19041d75c229d44
出典データセット
uspto-grants-2016_08
特許番号
US09428502B2

反応ノート

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