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

HRID 1696285ノート

反応式

HRID 1696285 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.[C:26](Cl)(=[O:28])[CH3:27].Cl>C(Cl)Cl>[C:26]([N:19]1[CH2:20][CH:15]([CH2:14][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:16][CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18]1)(=[O:28])[CH3:27]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66844627Ethyl 5-(cyclohexylmethyl)piperidine-3-carboxylate

生成物 1

HCID 66844834Ethyl 1-acetyl-5-(cyclohexylmethyl)piperidine-3-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Triethylamine (410 μL, 2.9 mmol) was added to a solution of ethyl 5-(cyclohexylmethyl)piperidine-3-carboxylate (180 mg, 0.71 mmol) and acetyl chloride (120 mg, 1.4 mmol) in CH2Cl2 (10 mL). The reaction was maintained at room temperature for 30 min before being diluted with CH2Cl2 (20 mL) and poured into HCl (1 N, 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 and purification by silica gel chromatography (hexane→80% EtOAc/hexane) provided the title compound as a yellow oil. MS m/z: 296.1 (M+1).

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  3. washThe combined organic layers were sequentially washed with H2O (10 mL) and brine
  4. dry with materialbefore being dried over Na2SO4
  5. concentrationConcentration
  6. customunder reduced pressure and purification by silica gel chromatography (hexane→80% EtOAc/hexane)

出典と根拠

ORDレコード
ord-ff1dad69d0334471b90cb9ecf74a01cf
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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