Pyridine → 3-(Cyanodiphenylmethyl)-1-pyrrolidinecarboxylic acid, methyl ester

HRID 1193497

반응식

HRID 1193497 반응식
C([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]#[N:15])[CH2:9]1)C1C=CC=CC=1.N1C=CC=CC=1.Cl[C:35]([O:37][CH3:38])=[O:36]>C(Cl)Cl>[C:14]([C:13]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:10]1[CH2:11][CH2:12][N:8]([C:35]([O:37][CH3:38])=[O:36])[CH2:9]1)#[N:15]

참가 물질

5

반응물 3

HCID 1049Pyridine2회HCID 6586Methyl chloroformate2회HCID 13633740alpha-(1-Benzyl-3-pyrrolidinyl)-alpha,alpha-diphenylacetonitrile

생성물 1

HCID 136337773-(Cyanodiphenylmethyl)-1-pyrrolidinecarboxylic acid, methyl ester수율 68.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 36.5 g (0.10 mole) of α-(1-benzyl-3-pyrrolidinyl)-α,α-diphenylacetonitrile and 8.7 g (0.11 mole) of pyridine in methylene chloride was added dropwise at 25° C., 10.4 g (0.11 mole) of methyl chloroformate. The solution was refluxed for 16 hr. To the refluxing solution was added 26.1 g (0.33 mole) of pyridine and 31.2 g (0.33 mole) additional methyl chloroformate. Heating at reflux was continued for 5 hr. The mixture was cooled and washed four times with water. The methylene chloride layer was dried and concentrated in vacuo. The residual oil was crystallized twice from a mix of petroleum ether (30°-60° ) and isopropanol to give 22 g (68%) of title product, m.p. 133°-135° C.

후처리

  1. temperatureThe solution was refluxed for 16 hr
  2. temperatureHeating
  3. temperatureat reflux
  4. temperatureThe mixture was cooled
  5. washwashed four times with water
  6. dry with materialThe methylene chloride layer was dried
  7. concentrationconcentrated in vacuo
  8. customThe residual oil was crystallized twice from
  9. additiona mix of petroleum ether (30°-60° ) and isopropanol

출처 및 근거

ORD 기록
ord-5cafb4c1829f42f9ad148b845911e957
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04810703

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