Trifluoroacetic acid → 4-(Azetidine-1-carbonyl)piperidine

HRID 426084ノート

反応式

HRID 426084 の反応式
[N:1]1([C:5]([CH:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)=[O:6])[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[N:1]1([C:5]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[O:6])[CH2:2][CH2:3][CH2:4]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 23658779tert-Butyl 4-[(azetidin-1-yl)carbonyl]piperidine-1-carboxylate

生成物 1

HCID 236587804-(Azetidine-1-carbonyl)piperidine収率 102.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

tert-Butyl 4-(azetidin-1-ylcarbonyl)piperidine-1-carboxylate (0.50 g, 1.86 mmol) was dissolved in methylene chloride (10 mL) and to the solution was added trifluoroacetic acid (2.12 g, 18.6 mmol). The mixture was stirred at RT overnight and then the solvent was removed by evaporation. The residue was dissolved in a small amount of methanol and THF and the solution was then loaded on a cation exchange sorbent (Isolute® SCX-2; 10 g). The column washed with THF and the product was then eluted with ammonia saturated methanol. The solvent was removed by evaporation. There was obtained 0.32 g (100%) of 4-(azetidin-1-ylcarbonyl)piperidine. 1H NMR (500 MHz, CDCl3): 1.4-1.5 (m, 4H), 2.0-2.2 (m, 3H), 2.4-2.5 (m, 2H), 2.9-3.0 (d, 2H), 3.7-3.8 (t, 2H), 3.9 (s, 1H), 4.0 (t, 2H).

後処理

  1. customthe solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in a small amount of methanol and THF
  3. washThe column washed with THF
  4. washthe product was then eluted with ammonia saturated methanol
  5. customThe solvent was removed by evaporation

出典と根拠

ORDレコード
ord-0a8d6dea2fee4d158928244235de5d67
出典データセット
uspto-grants-2012_01
特許番号
US08106208B2

反応ノート

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