- Synthesis of (S)-(+)-cericlamine through lipase-catalyzed aminolysis of azo acetates
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The kinetic enzymatic resolution of azo acetates via aminolysis with Candida antarctica lipase B has been investigated using benzylamine as amine component. The products obtained from this biotransformation in high enantiomeric purity can serve as valuable precursors for various amino alcohols, as exemplified by the synthesis of the serotonin reuptake inhibitor (S)-(+)-cericlamine.
- Prechter, Agnes,Groeger, Harald,Heinrich, Markus R.
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supporting information; experimental part
p. 3384 - 3387
(2012/06/01)
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- Non-enzymatic diastereoselective asymmetric desymmetrization of 2-benzylserinols giving optically active 4-benzyl-4-hydroxymethyl-2- oxazolidinones: Asymmetric syntheses of α-(hydroxymethyl)phenylalanine, N-Boc-α-methylphenylalanine, cericlamine and BIRT-377
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A reaction of (S)-2-benzyl-2-(α-methylbenzyl)amino-1,3-propanediol (S)-4a and 2-chloroethyl chloroformate, and the subsequent addition of DBU gave (4R,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone (4R)-5a (92% de) via a diastereoselective asymmetric desymmetrization process. Debenzylation of (4R)-5a using trifluoromethanesulfonic acid and anisole in MeNO2 gave (R)-4-benzyl-4-hydroxymethyl-2-oxazolidinone (R)-15a, which was converted into (R)-(α-hydroxymethyl)phenylalanine (7) in two steps. N-Boc-α-methylphenylalanine (8), cericlami0ne (9) and BIRT-377 (10) were also synthesized using these asymmetric desymmetrization and debenzylation.
- Sugiyama, Shigeo,Arai, Satoshi,Ishii, Keitaro
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p. 8033 - 8045
(2012/10/07)
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- Process for the preparation of (+/-)3-(3,4-dichlorophenyl)-2-dimethylamino-2-methylpropan-1-OL or cericlamine (INN)
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PCT No. PCT/EP98/02213 Sec. 371 Date Dec. 20, 1999 Sec. 102(e) Date Dec. 20, 1999 PCT Filed Apr. 6, 1998 PCT Pub. No. WO98/45248 PCT Pub. Date Oct. 15, 1998Process for the preparation of cericlamine which consists: i) in arylating methacrylic acid with th
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- Highly diastereoselective addition of Grignard reagents to aliphatic, enolizable N-alkylketimines and 2,2-disubstituted 1,3-oxazolidines. Asymmetric synthesis of the antidepressant cericlamine
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Grignard reagents were added to 2,2-disubstituted 1,3-oxazolidines and enolizable ketimines prepared from hydroxyacetone and phenylglycinol derivatives, with high to excellent diastereoselectivity, to yield 2,2- disubstituted 1,2-amino alcohol derivatives. Lewis acids had considerable influence on the yield and diastereoselectivity of the addition. This method was applied to the first asymmetric synthesis of the 5-HT reuptake inhibitor Cericlamine.
- Steinig,Spero
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p. 2406 - 2410
(2007/10/03)
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- Chemo-Enzymatic Synthesis of (S)-(+)-Cericlamine and Related Enantiomerically Pure 2,2-Disubstituted-2-aminoethanols
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The synthesis of (S)-(+)-cericlamine (S)-1 and related disubstituted amino alcohols is described as an example of the stereoselective synthesis of amino alcohols from disubstituted amino acids and their corresponding amides.Thus, the amino alcohols (S)-1,
- Kaptein, Bernard,Moody, Harold M.,Broxterman, Quirinus B.,Kamphuis, Johan
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p. 1495 - 1498
(2007/10/02)
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- Aminoalcohols, their preparation process and their applications, particularly in therapeutics
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Aminoalcohols of formula: STR1 in which R1 is alkyl, R2 H or alkyl, R3 in particularly H, alkyl, phenylakyl, alkanoyl, phenylalkanoyl, in which N, R2 and R3 together form a heterocycle saturated with
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