Improved Preparation of ( R ) and ( S )-3-Aminoquinuclidine Dihydrochloride
β Scribed by Kowalczyk, Bruce A.; Rohloff, John C.; Dvorak, Charles A.; Gardner, John O.
- Book ID
- 118232595
- Publisher
- Taylor and Francis Group
- Year
- 1996
- Tongue
- English
- Weight
- 260 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0039-7911
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π SIMILAR VOLUMES
3-Aminoquinuclidine, an important fragment associated with many 5-HT (serotonin) receptor ligands, has been synthesized using a 14Ccarbonation based sequence to prepare the starting material, isonicotinic 14C-acid (6). Elaboration of (6) to a-br~moacetyl-['~C] isonipecotic acid (Lp) via the correspo
S)-3-Aminoquinuclidine-3H 1 Oc-S having a specific activity of 66 Ci/mrnol was prepared in eight steps from lsonicotinic acid (2). Reduction of 2 with carrier free tritium gas over PtO2 In DMF gave isonipecotic acid-3H &. Conversion to a-bromo ketone followed by cyclization afforded 3-quinuclidone-
R) and (S)-3-aminoquinuclidines-3H with the specific activity of 35 Ci/mmol were prepared. Reduction of enamide 2 with carrier free tritium gas over RhCODCl dimer, (2S, 3s) Chiraphos in methanol gave yacemk amide &. Hydrolysis followed by resolution of the enantiomers with (R)-methyl benzyl isocyana
I n o r d e r t o s t u d y some a s p e c t s of t h e c e n t r a l metabolism of h i s t a m i n e r 3 3 w e have prepared N -[ H]methylhistamine d i h y d r o c h l o r i d e from [ Hlmethyl i o d i d e by chemical s y n t h e s i s and NT-methyl [a,8,2,4,5-14C51histamine d i h y d r o c h l o r