Sodium Carbonate → 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

HRID 343523Notes

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:61]=[CH:60][C:59]([N:62]2[CH:66]=[N:65][N:64]=[N:63]2)=[CH:58][C:54]=1[C:55](Cl)=[O:56]>C(OCC)(=O)C.O>[CH3:51][O:52][C:53]1[CH:61]=[CH:60][C:59]([N:62]2[CH:66]=[N:65][N:64]=[N:63]2)=[CH:58][C:54]=1[C:55]([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:56]

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 portionwise 2-methoxy-5-(1H-tetrazol-1-yl)benzoyl chloride (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, 1M aqueous hydrochloric acid solution, and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound. Rf =0.48 (9/1 dichloromethane/methanol).

Workup

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

Sources & evidence

ORD record: ord-beda92ec88e7426397aaf12b2aa85ce9
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05861417

Reaction notes

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