1-Pyrrolidineethanol → HCID 19891977, compound

HRID 893273Notes

Reaction equation

HRID 893273 reaction equation
[N:1]1([CH2:6][CH2:7][OH:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li]CCCC.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:23](Cl)=[O:24])=[CH:15]1>C1COCC1.CCCCCC>[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:23]([O:8][CH2:7][CH2:6][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:24])=[CH:15]1

Participants

6

Reactant 3

HCID 762881-PyrrolidineethanolHCID 123802781H-Indole-3-carbonyl chlorideHCID 178418339Butyllithium

Product 1

HCID 19891977HCID 19891977, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a dry THF solution of 2-(1-pyrrolidinyl)ethanol (1.10 g, 9.6 mmol) was dropwise added under ice-cooling a 1.5M hexane solution of n-BuLi (6.4 ml, 9.6 mmol) over a period of 10 min. followed by stirring for 30 min. The solvent was removed under reduced pressure. To the residue was added dry THF (20 ml). To the resulting pale yellow suspension was added a dry THF solution (5 ml) of indole-3-carboxylic acid chloride (1.00 g, 5.6 mmol) with stirring at room temperature over a period of 10 min. After stirring overnight, a reaction solution was then concentrated under reduced pressure. The residue was extracted with diluted hydrochloric acid followed by washing with ether. The aqueous layer was adjusted with saturated aqueous sodium bicarbonate to a pH of >10 and again extracted with ether. The organic layer was washed successively with water and saturated aqueous sodium chloride, then dried (MgSO4) and concentrated under reduced pressure to give 1.10 g of the title compound as colorless plates. m.p. 145°-146° C.;

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionTo the residue was added dry THF (20 ml)
  3. stirringwith stirring at room temperature over a period of 10 min
  4. stirringAfter stirring overnight
  5. concentrationa reaction solution was then concentrated under reduced pressure
  6. extractionThe residue was extracted with diluted hydrochloric acid
  7. washby washing with ether
  8. extractionagain extracted with ether
  9. washThe organic layer was washed successively with water and saturated aqueous sodium chloride
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-773836436a634c2fbed2f0b5bb10bebe
Source dataset
uspto-grants-1992_06
Patent number
US05124324

Reaction notes

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