Thiazole → Tert-butyl 4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]piperidine-1-carboxylate

HRID 1040006ノート

反応式

HRID 1040006 の反応式
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](=[O:26])[CH3:25])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>C1COCC1>[OH:26][C:24]([CH:21]1[CH2:20][CH2:19][N:18]([C:16]([O:15][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:17])[CH2:23][CH2:22]1)([C:7]1[S:6][CH:10]=[CH:9][N:8]=1)[CH3:25]

参加物

5

反応物 3

HCID 9256ThiazoleHCID 109879834-Acetyl-piperidine-1-carboxylic acid tert-butyl esterHCID 178418339Butyllithium

生成物 1

HCID 67431095Tert-butyl 4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]piperidine-1-carboxylate収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

n-Butyl lithium (0.281 mL, 0.702 mmol) was added dropwise to a stirred, cooled (−78° C.) mixture of thiazole (0.050 mL, 0.702 mmol) in THF (2.55 mL) and the mixture was stirred at −78° C. for 30 min. A solution of 4-acetyl-piperidine-1-carboxylic acid tert-butyl ester in THF (0.638 mL) was then added dropwise. Temperature was maintained at −78° C. for 30 min and then allowed to reach room temperature. The reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (×2). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography to give tert-butyl 4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]piperidine-1-carboxylate (180 mg, 0.576 mmol, 90%) as a colorless oil.

後処理

  1. temperaturecooled
  2. temperatureTemperature was maintained at −78° C. for 30 min
  3. customto reach room temperature
  4. customThe reaction was quenched with saturated NH4Cl solution
  5. extractionextracted with EtOAc (×2)
  6. washThe combined organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-4336c0d519ff43768e5ea8d48999b5d5
出典データセット
uspto-grants-2013_10
特許番号
US08551984B2

反応ノート

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