Chloroacetaldehyde → Tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate

HRID 253982ノート

反応式

HRID 253982 の反応式
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=[S:3])[NH2:2].Cl[CH2:18][CH:19]=O>CC(C)=O>[S:3]1[CH:19]=[CH:18][N:2]=[C:1]1[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

参加物

4

反応物 2

HCID 33Chloroacetaldehyde2 回HCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylate

生成物 1

HCID 58179889Tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of tert-butyl 4-thiocarbamoylpiperidine-1-carboxylate (1 g, 4.09 mmol) in acetone (5 mL) was added 2-chloroacetaldehyde (0.32 g, 4.08 mmol). The mixture was heated under reflux for 4 hours. Additional 2-chloroacetaldehyde (0.32 g, 4.08 mmol) was added and heating was continued for another 14 hours. The solvent was removed by evaporation and the crude product was purified by silica gel chromatography to give tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate as an oil [530 mg (1.97 mmol); LC-MS=213.1 (M+H); 1H NMR (300 MHz, CDCl3) 7.74 (d, J=3.3 Hz, 1H), 7.26 (d, J=3.3 Hz, 1H), 4.23 (brd, 2H), 3.22 (m, 1H), 2.91 (t, 2H), 2.14 (m, 2H), 1.77 (m, 2H), 1.48 (s, 9H)].

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureheating
  4. customThe solvent was removed by evaporation
  5. customthe crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-89ac6dc4724d42c688b61ccf506d6284
出典データセット
uspto-grants-2011_01
特許番号
US07872031B2

反応ノート

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