1983
DOI: 10.1071/ch9830601
|View full text |Cite
|
Sign up to set email alerts
|

Synthesis of analogues of GABA. VIII. Selective a-alkylation and γ-halogenation of the dianion from α,β-unsaturated nipecotic acid derivatives

Abstract: 1,2,3,6-Tetrahydropyridine-3-carboxylic acid (3), the β, γ-unsaturated derivative of the GABA uptake inhibitor nipecotic acid (1), has been synthesized by deconjugation via the dilithium salt of the N-t-butyloxycarbonyl-protected intermediate (6). Substitution of the intermediate with alkylating agents or an aldehyde gave predominantly a-alkylated products but chlorination with N-chlorosuccinimide provided a route to the γ-substituted unsaturated amino acid (13a).

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
3
2

Citation Types

0
7
0

Year Published

1983
1983
2000
2000

Publication Types

Select...
8

Relationship

0
8

Authors

Journals

citations
Cited by 15 publications
(7 citation statements)
references
References 0 publications
0
7
0
Order By: Relevance
“…It is known that arecoline (3) can be demethylated in high yields with various reagents including α-chloroethyl chloroformate 3 and 2,2,2-trichloroethyl chloroformate (TrocCl). 4 It is also known that the double bond in arecoline can be isomerised. 4, 5 It therefore seemed straightforward to perform these two steps and reduce the ester, thereby obtaining a potential precursor to isofagomine and its galacto analogue.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…It is known that arecoline (3) can be demethylated in high yields with various reagents including α-chloroethyl chloroformate 3 and 2,2,2-trichloroethyl chloroformate (TrocCl). 4 It is also known that the double bond in arecoline can be isomerised. 4, 5 It therefore seemed straightforward to perform these two steps and reduce the ester, thereby obtaining a potential precursor to isofagomine and its galacto analogue.…”
Section: Resultsmentioning
confidence: 99%
“…4, 5 It therefore seemed straightforward to perform these two steps and reduce the ester, thereby obtaining a potential precursor to isofagomine and its galacto analogue. Arecoline could be isomerised by following the known procedure 4 to give a 20 : 1 ratio of 4 and arecoline (3) in a quantitative yield (Scheme 1). The isomerized product 4 could not be separated chromatographically from the 5% content of arecoline (3) and was therefore used as such in the next step.…”
Section: Resultsmentioning
confidence: 99%
“…In 1983, Allan and Fong reported the successful N-demethylation of 1 using (2,2,2-trichloroethoxy)carbonyl chloride . However, the intermediate (trichloroethyl)carbamate was known to be sensitive to dialkylamide bases, which posed limits on subsequent alkylation experiments we envisioned.…”
Section: Resultsmentioning
confidence: 99%
“…NMR spectra were recorded at room temperature. Arecoline 1 was prepared from commercially available arecoline hydrobromide (Aldrich Chemical Co.) using a known procedure …”
Section: Methodsmentioning
confidence: 99%
“…Ater workup, arecoline (6) was distilled off from the remaining oil in vacuo and the resulting gum was treated with ethyl acetate to give 10a (556 mg, 52%) as colorless crystals: mp 107-108 °C; IR (KBr) 1715 (s) cm"1; NMR (CDCla) 7. 19 (1 H, m), 5.05 (1 H, br s), 3.72…”
Section: Methodsmentioning
confidence: 99%