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

HRID 1981906Notes

Reaction equation

HRID 1981906 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0741a03905ac45bd915acbd21d9095b5
Source dataset
uspto-grants-1986_06
Patent number
US04594343

Reaction notes

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