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

HRID 1029906Notes

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 2-(2-bromophenyl)acetic acid (10.7 g), pyrrolidine (20 cc) and copper acetate (1.66 g) is heated for 2 hours, with stirring, at 90° C.; after returning to ambient 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 1,2-dichloroethane (1,000 cc) and then with mixtures of 1,2-dichloroethane and methanol [(proportions by volume): 1,000 cc (98/2), 2,000 cc (97/3), 1,000 cc (96/4) and 1,000 cc (95/5)] and collecting 250 cc fractions. Fractions 21 to 29 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 2-[2-(1-Pyrrolidinyl)phenyl]acetic acid (2 g) is obtained in the form of an orange oil.

Workup

temperatureis heated for 2 hours
customafter returning to ambient temperature
concentrationthe 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 1,2-dichloroethane (1,000 cc)
customwith mixtures of 1,2-dichloroethane and methanol [(proportions by volume): 1,000 cc (98/2), 2,000 cc (97/3), 1,000 cc (96/4) and 1,000 cc (95/5)] and collecting 250 cc fractions
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-da98d0a794cd4f70ac9278e20d5d3eb3
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102667

Reaction notes

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