Water → 3-(3,4-Dimethoxyphenyl)-3-(2-hydroxyethyl)pyrrolidine

HRID 323186Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][C:12]1([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[CH2:16][C:15](=O)[NH:14][CH2:13]1)C.O.[OH-].[Na+]>O1CCCC1>[CH3:27][O:26][C:20]1[CH:19]=[C:18]([C:12]2([CH2:11][CH2:10][OH:9])[CH2:16][CH2:15][NH:14][CH2:13]2)[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

Participants

Conditions

Temperature: 10 °C

Procedure

Combine lithium aluminum hydride (0.99 g, 26.0 mmol) and anhydrous tetrahydrofuran (20 mL). Slowly, add (3-(3,4-dimethoxyphenyl)-5-oxopyrrolidin-3-yl)acetic acid ethyl ester (2.0 g, 6.5 mmol) as a solution in anhydrous tetrahydrofuran (40 mL). After the addition is complete, heat to reflux. After 18 hours, cool in an ice-bath. Add water (1 mL) dropwise at such a rate that the temperature of the reaction mixture does not rise above 20° C. Cool to 10° C., add 15% sodium hydroxide solution (1.0 mL). Add water (3 mL). After 15 minutes, filter the reaction mixture and concentrate the filtrate in vacuo to give the title compound: Rf=0.68 (silica gel, 5/1 ethyl acetate/methanol).

Workup

additionAfter the addition
temperatureheat to reflux
temperaturecool in an ice-bath
customdoes not rise above 20° C
waitAfter 15 minutes
filtrationfilter the reaction mixture
concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record: ord-10691865eee446b7a0aebb3f96de0d32
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211199B1

Reaction notes

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