Sodium Carbonate → 1-(3,4,5-Trimethoxybenzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

HRID 323241Notes

Reaction equation

C([C@](C(O)=O)(O)[C@](C(=O)C1C=CC(OC)=CC=1)(O)C(O)=O)(=O)C1C=CC(OC)=CC=1.[C:31]1([C:37]2([CH2:42][CH2:43][OH:44])[CH2:41][CH2:40][NH:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:51][O:52][C:53]1[CH:54]=[C:55]([CH:59]=[C:60]([O:64][CH3:65])[C:61]=1[O:62][CH3:63])[C:56](Cl)=[O:57]>C(OCC)(=O)C.O>[CH3:65][O:64][C:60]1[CH:59]=[C:55]([CH:54]=[C:53]([O:52][CH3:51])[C:61]=1[O:62][CH3:63])[C:56]([N:39]1[CH2:40][CH2:41][C:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([CH2:42][CH2:43][OH:44])[CH2:38]1)=[O:57]

Participants

Conditions

Temperature: 0 °C

Procedure

Combine (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt (56.0 g, 92.1 mmol), sodium carbonate (19.5 g, 184 mmol) in ethyl acetate (2 L) and water (2 L). Cool to about 0° C. in an ice bath. After 30 minutes, slowly add dropwise portionwise 3,4,5-trimethoxybenzoyl chloride (21.2 g, 92.1 mmol). After the addition is complete, warm to ambient temperature. After 1 hour, dilute the reaction mixture ethyl acetate and extract with water, 1 M aqueous hydrochloric acid solution, and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

additionAfter the addition
temperaturewarm to ambient temperature
waitAfter 1 hour
extractionextract with water, 1 M aqueous hydrochloric acid solution
dry with materialDry the organic layer over Na2SO4
filtrationfilter
customevaporate in vacuo

Sources & evidence

ORD record: ord-330aea5e32dc464c9386029bbf45305b
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211199B1

Reaction notes

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