Pyrrolidine → 4-Pyrrolidin-1-ylnaphthalene-1-carboxylic acid ethyl ester

HRID 916317Notes

Reaction equation

HRID 916317 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](F)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 69226285HCID 69226285, compound

Product 1

HCID 115072934-Pyrrolidin-1-ylnaphthalene-1-carboxylic acid ethyl esterYield 70%

Procedure

154BG85-11 (156 mg, 0.7 mmol) was transferred to a Pyrex tube and pyrrolidine (1 mL) was added. The tube was capped and the reaction tube was exposed to microwave irradiation (100° C., 3 min). The microwave exposure was repeated for 5 min at 130° C. The pyrrolidine was evaporated and the reaction mixture was transferred to a separation funnel with ethyl acetate and washed with 2 M NaOH. The aqueous phase was acidified with 2 M HCl and extracted with ethyl acetate. The organic phases were collected, dried over Na2SO4, filtered and concentrated to yield 135 mg (70%) of the title compound.

Workup

  1. additionwas added
  2. customThe tube was capped
  3. customthe reaction tube was exposed to microwave irradiation (100° C., 3 min)
  4. customThe pyrrolidine was evaporated
  5. customthe reaction mixture was transferred to a separation funnel with ethyl acetate
  6. washwashed with 2 M NaOH
  7. extractionextracted with ethyl acetate
  8. customThe organic phases were collected
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-142e262cbb384408977646cb6917763c
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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