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

HRID 253104노트

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HRID 253104 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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 (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 provided the title compound. MS m/z: 332.1 (M+1).

후처리

  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

출처 및 근거

ORD 기록
ord-7c2aed39b60548619ac1c74a43753772
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872009B2

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