20069-02-7

Basic information

• Product Name: 1-Methyl-4-[(2S)-1-methyl-2α-pyrrolidinyl]-β-carboline
• Synonyms: (-)-1-Methyl-4-[(2S)-1-methyl-2-pyrrolidinyl]-9H-pyrido[3,4-b]indole;(-)-Brevicolline;(S)-Brevicolline;1-Methyl-4-[(2S)-1-methyl-2α-pyrrolidinyl]-9H-pyrido[3,4-b]indole;1-Methyl-4-[(2S)-1-methyl-2α-pyrrolidinyl]-β-carboline;Brevicolline
• CAS NO: 20069-02-7
• Molecular Formula: C17H19N3
• Molecular Weight: 265.35286
• Mol File: 20069-02-7.mol

Chemical Properties

• Boiling Point: 459.4°C at 760 mmHg
• Flash Point: 231.6°C
• Appearance: /
• Density: 1.206g/cm³
• Vapor Pressure: 1.27E-08mmHg at 25°C
• Refractive Index: 1.691
• CAS DataBase Reference: 1-Methyl-4-[(2S)-1-methyl-2α-pyrrolidinyl]-β-carboline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-4-[(2S)-1-methyl-2α-pyrrolidinyl]-β-carboline(20069-02-7)
• EPA Substance Registry System: 1-Methyl-4-[(2S)-1-methyl-2α-pyrrolidinyl]-β-carboline(20069-02-7)

Safety Data

• Hazardous Substances Data: 20069-02-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H19N3/c1-11-17-16(12-6-3-4-7-14(12)19-17)13(10-18-11)15-8-5-9-20(15)2/h3-4,6-7,10,15,19H,5,8-9H2,1-2H3

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Relevant articles and documents

Synthesis of enantiomerically pure (-)-(S)-brevicolline

(-)-(S)-Brevicolline (1) and related β-carbolines were synthesized using an enantiomerically pure Michael-acceptor synthon (3). Subsequent Pictet-Spengler reaction afforded the tetrahydro-β-carboline skeleton, which, in turn, was transformed to the β-carboline by catalytic dehydrogenation.

Synthesis of Racemic and Enantiopure Forms of β-Carboline Alkaloid Brevicolline

A new total synthesis of the pharmacologically active β-carboline alkaloid brevicolline is described. The new synthetic approach is based on a commercially available and inexpensive starting material and reagents leading to a practical synthesis of the racemic target molecule, the natural (S)-enantiomer, and its antipode. Initially, the construction of the β-carboline skeleton and functionalization at the C(4) position have been accomplished. The formation of dihydropyrrole structural unit was obtained as the result of an Au-catalyzed hydroamination reaction, which was followed by a reduction that led to the chiral intermediate. The synthetic route described here is developed to ensure the sustainable access of the racemic brevicolline in 11 steps with improved 48% overall yield compared to the previously reported methods.

SYNTHESIS AND REGIOSELECTIVE SUBSTITUTION OF 6-HALO-AND 6-ALKOXY NICOTINE DERIVATIVES

The present invention provides active compounds for modulating nicotinic acetylcholine receptors and methods of making the same. The methods of preparing the active compounds utilize different intermediate compounds.

Six-step synthesis of (S)-brevicolline from (S)-nicotine

A six-step synthesis of (S)-brevicolline from (S)-nicotine is reported. Regioselective trisubstitution of the pyridine ring of nicotine, followed by successive Suzuki cross-coupling and Buchwald animation reactions, afforded the enantiopure β-carboline al