Dichloromethane → 1-Benzylpyrrolidine-3-carbaldehyde

HRID 2050186

Reaction equation

HRID 2050186 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([N:23]1[CH2:27][CH2:26][CH:25]([CH2:28][OH:29])[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.P(Cl)(Cl)(Cl)(Cl)Cl.C(Cl)Cl>CS(C)=O>[CH2:16]([N:23]1[CH2:27][CH2:26][CH:25]([CH:28]=[O:29])[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10868Dicyclohexylcarbodiimide2×HCID 24819Phosphorus pentachlorideHCID 5176654(1-Benzylpyrrolidin-3-yl)methanol

Product 1

HCID 45894781-Benzylpyrrolidine-3-carbaldehydeYield 66%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 61.8 g (0.3 mole) of dicyclohexylcarbodiimide in 400 ml of dry dimethylsulfoxide is dropwise added a solution of 19.10 g (0.1 mole) of 1-benzyl-3-hydroxymethylpyrrolidine [prepared in the manner described in J. O. C. 26, 1519 (1961) by YAO-HUA WU and R. F Feldkamp] under ice-cooling for 15 minutes, and the mixture is stirred at room temperature overnight. Dicyclohexylcarbodiimide (13.26 g; 60 mmoles) and phosphorus pentachloride (4.40 g; 30 mmoles) are added thereto and the mixture is stirred overnight, poured into ice water, mixed with 300 ml of methylene chloride and stirred for 30 minutes. The insoluble materials, which appear, are filtered off and washed with water. The combined filtrate and washings are washed twice with 200 ml of methylene chloride, adjusted to pH 9 with 20 (w/w) % aqueous sodium carbonate solution, and extracted four times with 200 ml of methylene chloride. The extract is washed with 20 (w/w) % aqueous sodium hydrogensulfite solution. The aqueous layer is separated, washed thrice with 100 ml of methylene chloride, mixed with 20 (w/w) % aqueous sodium carbonate solution, and extracted with methylene chloride. The extract is washed with water, dried over sodium sulfate and evaporated under reduced pressure to yield crude oily 1-benzyl-3-formylpyrrolidine in 66% yield.

Workup

  1. customprepared in the manner
  2. temperatureF Feldkamp] under ice-cooling for 15 minutes
  3. stirringthe mixture is stirred overnight
  4. stirringstirred for 30 minutes
  5. filtrationare filtered off
  6. washwashed with water
  7. washThe combined filtrate and washings are washed twice with 200 ml of methylene chloride
  8. extractionextracted four times with 200 ml of methylene chloride
  9. washThe extract is washed with 20 (w/w) % aqueous sodium hydrogensulfite solution
  10. customThe aqueous layer is separated
  11. washwashed thrice with 100 ml of methylene chloride
  12. additionmixed with 20 (w/w) % aqueous sodium carbonate solution
  13. extractionextracted with methylene chloride
  14. washThe extract is washed with water
  15. dry with materialdried over sodium sulfate
  16. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-39fcd3c9ac6b4bf2ae7f201216d33f9d
Source dataset
uspto-grants-1980_04
Patent number
US04200628

Linked notes

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