Triethylamine → (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide

HRID 1632555노트

반응식

HRID 1632555 반응식
[I-].ClC1C=CC=C[N+]=1C.[C:10]([O:13][CH:14]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]([OH:22])=O)[C:15]1=[O:23])(=[O:12])[CH3:11].[CH3:24][C@H:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([CH3:31])[N:26]1[CH2:32][CH2:33][NH2:34].C(N(CC)CC)C>C(Cl)Cl>[CH3:24][C@H:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([CH3:31])[N:26]1[CH2:32][CH2:33][NH:34][C:20](=[O:22])[CH2:19][N:16]1[CH2:17][CH2:18][CH:14]([O:13][C:10](=[O:12])[CH3:11])[C:15]1=[O:23]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 7837022-(cis-2,6-Dimethyl-1-piperidinyl)ethanamineHCID 54389912(R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid

생성물 1

HCID 53715870(R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

1.81 g of 2-chloro-1-methyl-pyridinium iodide are suspended in 10 ml of methylene chloride and thereto there are added at room temperature 1.20 g of (R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid. Within 15 minutes there is added dropwise at 0° a solution of 0.98 g of 94.7% cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine and 3.02 ml of triethylamine in 20 ml of methylene chloride, whereupon the mixture is stirred at room temperature for 18 hours. Thereupon, the mixture is evaporated and the residue is chromatographed on aluminum oxide (activity grade III, neutral). The material which is eluted with chloroform is chromatographed on silica gel (granular size 0.2-0.5 mm). The (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with alcohol has a melting point of 120°-122° after crystallization from diethyl ether.

후처리

  1. customThereupon, the mixture is evaporated
  2. customthe residue is chromatographed on aluminum oxide (activity grade III, neutral)
  3. washThe material which is eluted with chloroform
  4. customis chromatographed on silica gel (granular size 0.2-0.5 mm)
  5. washThe (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with alcohol
  6. customafter crystallization from diethyl ether

출처 및 근거

ORD 기록
ord-a0e50868429e482aa661a3fec840958d
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04476308

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