101385-90-4Relevant articles and documents
Natural (-)-vasicine as a novel source of optically pure 1-benzylpyrrolidin-3-ol
Aga, Mushtaq A.,Kumar, Brijesh,Rouf, Abdul,Shah, Bhahwal A.,Andotra, Samar S.,Taneja, Subhash C.
, p. 969 - 977 (2013)
A facile and scalable methodology for the preparation of optically active (3S)-1-benzylpyrrolidin-3-ol (3), an important drug precursor, is reported. Starting from the naturally occurring alkaloid (-)-vasicine (1), a major alkaloid of the plant Adhatoda vasica, 3 was obtained in 84% overall yield (Scheme 3). Copyright
Inverting the enantioselectivity of P450pyr monooxygenase by directed evolution
Tang, Weng Lin,Li, Zhi,Zhao, Huimin
, p. 5461 - 5463 (2010)
We report the first example of directed evolution of a P450 monooxygenase with inverted enantioselectivity for asymmetric biohydroxylation. The biohydroxylation product of the best mutant 1AF4A has an ee of 83% (R) compared to the wild type's ee of 43% (S). The Royal Society of Chemistry 2010.
Hydroboration. 78. Reinvestigation of the Hydroboration of N-Substituted-3-pyrrolines. Preparation of N-Benzyl-3-pyrrolidinol and (N-Benzyl-3-pyrrolidinyl)boronate of Very High Enantiomeric Purity
Brown, Herbert C.,Prasad, J. V. N. Vara,Gupta, Ashok K.
, p. 4296 - 4298 (1986)
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Method (S)-3- for -1- synthesizing P-hydroxymethylbenzopyrrolidine (by machine translation)
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Paragraph 0027-0033, (2020/02/14)
After the completion of (S)- 3 - the dropwise addition of the solvent, the reaction liquid,S1, drops are added, into the solvent and then, refluxed, under the (S)- 3, conditions of the temperature under, the conditions 20-65 °C of, the. temperature of the temperature 4 - of the temperature of the reflux ;S2, of (S)4 - the reaction solution, 10-65 °C 10-12h;S3, (S)- 1 -S4, (S)- 1 - 0-65 °C 12-20h;S5, (S)- 3 . (by machine translation)
Preparation of enantiomerically pure N-heterocyclic amino alcohols by enzymatic kinetic resolution
Tofani, Giorgio,Petri, Antonella,Piccolo, Oreste
, p. 638 - 643 (2015/08/03)
Abstract The synthesis of both enantiomers of N-benzyl-3-hydroxypyrrolidine and N-benzyl-3-hydroxypiperidine via enzymatic kinetic resolution of the corresponding racemic esters is described. Various commercially available hydrolases were studied as biocatalysts in native and immobilized form. The best results were obtained with lipases PS, AK, CAL-B and with protease Alcalase, which were active and selective for the kinetic resolutions of racemic esters (E > 100). Under optimized reaction conditions, highly enantiomerically enriched (up to 99.5% ee) resolution products were obtained. Lipase and protease showed opposite enantiopreference on the esters, allowing the preparation of both enantiomers of the target compounds. Semi-continuous reactions in column reactors with immobilized biocatalysts were also performed with high enantioselectivities. Inversion of the configuration at C(3) of N-benzyl-3-hydroxypyrrolidine was quantitatively effected in a short number of steps.