1-Methyl-2-pyrrolidineethanol → HCID 19891945, compound

HRID 893275Notes

Reaction equation

HRID 893275 reaction equation
[CH3:1][N:2]1[CH:6]([CH2:7][CH2:8][OH:9])[CH2:5][CH2:4][CH2:3]1.[Li]CCCC.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24](Cl)=[O:25])=[CH:16]1>C1COCC1.CCCCCC>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24]([O:9][CH2:8][CH2:7][CH:6]2[CH2:5][CH2:4][CH2:3][N:2]2[CH3:1])=[O:25])=[CH:16]1

Participants

6

Reactant 3

HCID 933631-Methyl-2-pyrrolidineethanolHCID 123802781H-Indole-3-carbonyl chlorideHCID 178418339Butyllithium

Product 1

HCID 19891945HCID 19891945, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a dry THF solution (30 ml) of 2-(1-methyl-2-pyrrolidine)ethanol at -10° to 5° C. was dropwise added a 1.5M hexane solution of n-BuLi (16.0 ml, 24.0 mmol) over a period of 10 min. Stirring was continued for 30 min. To a mixture was then dropwise added at -5° to 5° C. a dry THF solution (20 ml) of indole-3-carboxylic acid chloride (4.20 g, 24.0 mmol) over a period of 45 min. The cooling bath was removed. After stirring overnight at room temperature, a reaction solution was poured onto a cold diluted hydrochloric acid, and the aqueous layer was washed with ethyl acetate. The aqueous layer was adjusted with saturated aqueous sodium bicarbonate to a pH of >10 and extracted with ethyl acetate. The organic layer was washed successively with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.91 g of the title compound as a yellow viscous material. A foamy solid;

Workup

  1. customThe cooling bath was removed
  2. stirringAfter stirring overnight at room temperature
  3. additiona reaction solution was poured onto a cold diluted hydrochloric acid
  4. washthe aqueous layer was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed successively with water and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b36f138b0f6248f0b3c44e8f9cfec26f
Source dataset
uspto-grants-1992_06
Patent number
US05124324

Reaction notes

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