A STUDY OF THE EFFECT OF CATALYST ON STEREOCHEMISTRY IN THE HYDROGENATION OF N-(MENTHYLOXYCARBONYL)-N-METHYL-2-(N-PYRROLIDINYL)-1-CYCLOHEXENAMINE

被引：3

作者：

MATECKA, D ^{[1
]}

DECOSTA, BR ^{[1
]}

机构：

[1] NIADDKD,MED CHEM LAB,9000 ROCKVILLE PIKE,BETHESDA,MD 20892

来源：

SYNTHETIC COMMUNICATIONS | 1994年 / 24卷 / 11期

关键词：

D O I：

10.1080/00397919408010153

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic hydrogenation of N-(menthyloxycarbonyl)-N-methyl-2-(1-pyrrolidinyl)-1-cyclohexenamine (3) gave mainly 1R,2S-cis-N-(menthyloxycarbonyl)- and 1S,2R-cis-N-(menthyloxycarbonyl)-N-methyl-2-(1-pyrrolidinyl)cyclohexylamines 7 and 8 with diasterostereoselectivity favoring the 1S,2R-isomer 8.

引用

页码：1531 / 1540

页数：10

共 9 条

[1] HIGHLY SELECTIVE KAPPA-OPIOID ANALGESICS - SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF NOVEL N-[(2-AMINOCYCLOHEXYL)ARYL]ACETAMIDE AND N-[(2-AMINOCYCLOHEXYL)ARYLOXY]ACETAMIDE DERIVATIVES [J].

CLARK, CR ;

HALFPENNY, PR ;

HILL, RG ;

HORWELL, DC ;

HUGHES, J ;

JARVIS, TC ;

REES, DC ;

SCHOFIELD, D .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (04) :831-836

[2] EVALUATION OF U-50,488H ANALOGS FOR NEUROPROTECTIVE ACTIVITY IN THE GERBIL [J].

CONTRERAS, PC ;

RAGAN, DM ;

BREMER, ME ;

LANTHORN, TH ;

GRAY, NM ;

IYENGAR, S ;

JACOBSON, AE ;

RICE, KC ;

DECOSTA, BR .

BRAIN RESEARCH, 1991, 546 (01) :79-82

[3] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF OPTICALLY PURE ENANTIOMERS OF A KAPPA-OPIOID RECEPTOR SELECTIVE AGONIST [J].

DECOSTA, B ;

GEORGE, C ;

ROTHMAN, RB ;

JACOBSON, AE ;

RICE, KC .

FEBS LETTERS, 1987, 223 (02) :335-339

[4] ALTERATIONS IN THE STEREOCHEMISTRY OF THE K-SELECTIVE OPIOID AGONIST U50,488 RESULT IN HIGH-AFFINITY OMICRON-LIGANDS [J].

DECOSTA, BR ;

BOWEN, WD ;

HELLEWELL, SB ;

GEORGE, C ;

ROTHMAN, RB ;

REID, AA ;

WALKER, JM ;

JACOBSON, AE ;

RICE, KC .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (08) :1996-2002

[5]

GODCHOT M, 1932, B SOC CHIM FR, V51, P1277

[6] POSSIBLE CEREBROPROTECTIVE AND INVIVO NMDA ANTAGONIST ACTIVITIES OF SIGMA-AGENTS [J].

PONTECORVO, MJ ;

KARBON, EW ;

GOODE, S ;

CLISSOLD, DB ;

BOROSKY, SA ;

PATCH, RJ ;

FERKANY, JW .

BRAIN RESEARCH BULLETIN, 1991, 26 (03) :461-465

[7] SYNTHESIS AND RECEPTOR-BINDING OF ENANTIOMERIC N-SUBSTITUTED CIS-N-[2-(3,4-DICHLOROPHENYL)ETHYL]-2-(1-PYRROLIDINYL)CYCLOHEXYLAMINES AS HIGH-AFFINITY SIGMA RECEPTOR LIGANDS [J].

RADESCA, L ;

BOWEN, WD ;

DIPAOLO, L ;

DECOSTA, BR .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (10) :3058-3065

[8] NOVEL, ENANTIOSELECTIVE SYNTHESIS OF VICINAL CYCLOHEXANE-DIAMINES AS KEY-INTERMEDIATES FOR HIGHLY SELECTIVE OPIOID KAPPA-AGONIST AND SIGMA-AGONIST [J].

SCHLICHTER, WH ;

FRAHM, AW .

TETRAHEDRON-ASYMMETRY, 1992, 3 (03) :329-332

[9]

WALKER JM, 1990, PHARMACOL REV, V42, P355

← 1 →