Pyrrolidine → 2-[2-(Pyrrolidin-1-yl)phenyl]acetic acid

HRID 1599136Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N:12]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]([OH:11])=[O:10])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 10.7 g of 2-(2-bromophenyl)acetic acid, 20 cm3 of pyrrolidine and 1.66 g of copper acetate is heated at 90° C. with stirring for 2 hours; after return to room temperature, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 5 cm, height 55 cm), eluting with 1000 cm3 of 1,2-dichloroethane then with mixtures of 1,2-dichloroethane and methanol (proportions by volume): 1000 cm3 (98:2), 2000 cm3 (97:3), 1000 cm3 (96:4) and 1000 cm3 (95:5) and collecting fractions of 250 cm3. Fractions 21 to 29 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 2 g of 2-[2-(1-pyrrolidinyl)phenyl]acetic acid are obtained in the form of an orange-coloured oil.

Workup

concentrationafter return to room temperature, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
customThe residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 5 cm, height 55 cm)
washeluting with 1000 cm3 of 1,2-dichloroethane
customwith mixtures of 1,2-dichloroethane and methanol (proportions by volume): 1000 cm3 (98:2), 2000 cm3 (97:3), 1000 cm3 (96:4) and 1000 cm3 (95:5) and collecting fractions of 250 cm3
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-21b63453af7941acb025c9210b3ba33d
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739351

Reaction notes

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