Hydrochloric Acid → Ethyl 5-(cyclohexylmethyl)-1-(methylsulfonyl)piperidine-3-carboxylate

HRID 1696287ノート

反応式

HRID 1696287 の反応式
C(N(CC)CC)C.[CH:8]1([CH2:14][CH:15]2[CH2:20][NH:19][CH2:18][CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].Cl>C(Cl)Cl>[CH:8]1([CH2:14][CH:15]2[CH2:20][N:19]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:18][CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66844627Ethyl 5-(cyclohexylmethyl)piperidine-3-carboxylate

生成物 1

HCID 66844753Ethyl 5-(cyclohexylmethyl)-1-(methylsulfonyl)piperidine-3-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Triethylamine (340 mL, 2.4 mmol) was added to a solution of ethyl 5-(cyclohexylmethyl)piperidine-3-carboxylate (155 mg, 0.60 mmol) and methanesulfonyl chloride (75 mL, 0.90 mmol) in CH2Cl2 (6 mL) cooled to 0° C. The reaction was maintained at this temperature for 15 min at which point the whole was allowed to warm to RT and stir for an additional 3 h. The reaction was diluted with CH2Cl2 (20 mL) and poured into HCl (1N, 20 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were sequentially washed with H2O (10 mL) and brine before being dried over Na2SO4. Concentration under reduced pressure provided the title compound. MS m/z: 332.1 (M+1).

後処理

  1. temperatureThe reaction was maintained at this temperature for 15 min at which point the whole
  2. temperatureto warm to RT
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  5. washThe combined organic layers were sequentially washed with H2O (10 mL) and brine
  6. dry with materialbefore being dried over Na2SO4
  7. concentrationConcentration under reduced pressure

出典と根拠

ORDレコード
ord-c7193180698c49389f1ccc104d8c9b6f
出典データセット
uspto-grants-2012_04
特許番号
US08163766B2

反応ノート

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