A stereoselective approach to both 3,4-trans-disubstituted pyrrolidin-2-ones and pyrrolidines. A convenient synthesis of (3R,4R)-4-benzyl-3-pyrrolidinecarboxylic acid

Heterocycles

Volumn 60, Issue 11, 2003, Pages 2485-2498

  Galeazzi, Roberta ^a   Martelli, Gianluca ^a   Mobbili, Giovanna ^a   Orena, Mario ^a   Panagiotaki, Maria ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 (1' PHENYLETHYL) 3 PIVALOYLOXYMETHYL 4 TETRAHYDROPYRANYLOXYMETHYLPYRROLIDIN 2 ONE; 3 BENZYL 4 BENZYLOXYMETHYL 1 (1' PHENYLETHYL)PYRROLIDIN 2 ONE; 3 BENZYL 4 BENZYLOXYMETHYL 1 (1' PHENYLETHYL)PYRROLIDINE; 3 BENZYLOXYMETHYL 1 PHENYLETHYL 4 TETRAHYDROPYRANYLOXYMETHYLPYRROLIDIN 2 ONE; 3 METHOXYCARBONYL 1 PHENYLETHYL 4 TETRAHYDROPYRANYLOXYMETHYLPYRROLIDIN 2 ONE; 3,4 DIBENZYLOXYMETHYL 1 (1' PEHNYLETHYL)PYRROLIDIN 2 ONE; 3,4 DIBENZYLOXYMETHYL 1 (1' PHENYLETHYL)PYRROLIDINE; 4 BENZYL 3 BENZYLOXYMETHYL 1 TERT BUTOXYCARBONYLPYRROLIDINE; 4 BENZYL 3 PYRROLIDONECARBOXYLIC ACID; 4 BENZYLOXYMETHYL 3 ETHYL 1 (1' PHENYLETHYL)PYRROLIDIN 2 ONE; 4 BENZYLOXYMETHYL 3 ETHYL 1 (1' PHENYLETHYL)PYRROLIDINE; 4 TERT BUTYLDIMETHYLSILOXYMETHYL 1 (1' PHENYLETHYL) 3 PROPYLPYRROLIDIN 2 ONE; BENZYL DERIVATIVE; HYDROXYL GROUP; NITROGEN; PYRROLIDIN 2 ONE DERIVATIVE; PYRROLIDINE DERIVATIVE; SILYLOXYMETHYLPYRROLIDIN 2 ONE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0142027265     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-9854     Document Type: Article

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35. It is worth mentioning that good results were observed also when the (4S,1′R)-4-hydroxymethyl derivative (I), easily obtained starting from 7 according ref. 9, was converted into the corresponding benzyl ether (II) and subsequent alkylation reaction led to IIIa,b in good yield, thus allowing to prepare the diastereomers of compounds (11). (i. n-Buli. THF, then BnBr, 91% ii. n-Buli, THF 0°C. Then, for IIIa, BnBr, R = Bn, 91% and, for IIIb, EtI, R = Et, 87%).