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

HRID 1193497ノート

反応式

HRID 1193497 の反応式
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]

参加物

5

反応物 3

HCID 1049Pyridine2 回HCID 6586Methyl chloroformate2 回HCID 13633740alpha-(1-Benzyl-3-pyrrolidinyl)-alpha,alpha-diphenylacetonitrile

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5cafb4c1829f42f9ad148b845911e957
出典データセット
uspto-grants-1989_03
特許番号
US04810703

反応ノート

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