In 1957,Recueil des Travaux Chimiques des Pays-Bas et de la Belgique included an article by Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.. Formula: C7H14ClNO2. The article was titled 《Absolute configuration of sedamine and sedridine》. The information in the text is summarized as follows:
Synthetic 1-phenyl-2-(2-N-methylpiperidyl)ethanol (I) was previously separated into its 2-diastereoisomeric pairs, (±)-sedamine (Ia) and (±)-allosedamine (Ib) (cf. B. and Enthoven, C.A. 50, 13005i). By using Dg-(+)-dibenzoyltartaric acid, Ia, m. 89-90°, gave (+)-sedamine Dg-bis(dibenzoyltartrate) monohydrate, m. 133-4°, [α]D18 87.5 ± 1.7° (c 3.00, alc.), converted to (+)-sedamine, m. 61-2°, [α]D18 91.5 ± 1° (c 3.29, alc.) (not previously isolated from Sedum acre L.). Similar resolution of Ib through (-)-allosedamine Lg-bis(dibenzoyltartrate) monohydrate, m. 110-11°, [α]D18 -82.5 ± 1° (c 2.01, alc.) and (+)-allosedamine Dg-bis(dibenzoyltartrate) monohydrate, m. 112-13°, [α]D19 83.2 ± 1° (c 1.74, alc.) yielded (+)-allosedamine (Ic), m. 79-80°, [α]D20 18.6 ± 0.4° (c 2.42, alc.), and (-)-allosedamine (Id), m. 79-80°, [α]D21 -18.9 ± 0.9° (c 2.06, alc.); chloroaurate, m. 182-3°. Ic or Id is probably identical with the alkaloid, C14H21NO, of Wieland, et al. (C.A. 34, 1088). Ic and (-)-sedamine (II) refluxed 1 hr. with CrO3 in 4NH2SO4 gave (+)-N-methylpipecolic acid HCl salt, m. 211-12°, [α]D20 47.2 ± 0.8° (c 2.42, H2O), and (-)-N-methylpipecolic acid HCl salt, m. 211-12° [α]D20 47.2 ± 0.8° (c 2.42, H2O), identical with the HCl salts originating from the N-methylation of (-)- or (+)-pipecolic acid (III) with HCHO. III is related via the alkaloid baikiaine with L-aspartic acid (cf. King, et al., C.A. 45, 7083b) and accordingly, in II and Id, the arrangement of the bonds around the piperidine ring asym. C atom corresponds to the Ls configuration. The absolute configuration of the piperidine part of natural (+)-sedridine (IV), m. 83-4°, [α]D22 26° (c 1.28, alc.), [α]D20 286 ± 0.9° (c 2.28, alc.), may be deduced from the literature data and it would seem that the asym. center in the piperidine ring of IV also has the Ls configuration. These stereochem. findings are consistent with the conception of the origin of the piperidine portion of II and IV from L-amino acids. The experimental part of the paper was very detailed, including the reaction process of 1-Methylpiperidine-2-carboxylic acid hydrochloride(cas: 25271-35-6Formula: C7H14ClNO2)
1-Methylpiperidine-2-carboxylic acid hydrochloride(cas: 25271-35-6) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.Formula: C7H14ClNO2
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem