55812-46-9

Basic information

• Product Name: Pyridindolol
• Synonyms: (R)-α-Hydroxymethyl-9H-pyrido[3,4-b]indole-1,3-dimethanol;1-[(1R)-1,2-Dihydroxyethyl]-9H-pyrido[3,4-b]indole-3-methanol;Pyridindolol
• CAS NO: 55812-46-9
• Molecular Formula: C14H14 N2 O3
• Molecular Weight: 258.27
• Mol File: 55812-46-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 604.3°Cat760mmHg
• Flash Point: 319.3°C
• Appearance: /
• Density: 1.505g/cm³
• Vapor Pressure: 1.86E-15mmHg at 25°C
• Refractive Index: 1.802
• CAS DataBase Reference: Pyridindolol(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridindolol(55812-46-9)
• EPA Substance Registry System: Pyridindolol(55812-46-9)

Safety Data

• Hazardous Substances Data: 55812-46-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H14N2O3/c17-6-8-5-10-9-3-1-2-4-11(9)16-13(10)14(15-8)12(19)7-18/h1-5,12,16-19H,6-7H2

Upstream product

• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 189756-51-2 16-O-acetylpyridindolol 
• 189756-49-8 15,16-O-diacetylpyridindolol 
• 188037-57-2 3-iodo-1-(methoxymethyl)indole-2-carboxaldehyde 
• 304435-44-7 1-ethenyl-3-hydroxymethyl-9H-pyrido[3,4-b]indole 
• 304435-38-9 3-[3-(methoxymethyloxy)prop-1-yn-1-yl]-N-(methoxymethyl)indole-2-carbaldehyde 
• 304435-45-8 3-(acetoxy)methyl-1-ethenyl-9H-pyrido[3,4-b]indole 
• 304435-40-3 3-(methoxymethyloxy)methyl-N-methoxymethyl-9H-pyrido[3,4-b]indole N-oxide 
• 304435-39-0 3-[3-(methoxymethyloxy)prop-1-yn-1-yl]-N-(methoxymethyl)indole-2-carbaldehyde oxime 
• 304435-43-6 1-ethenyl-3-(methoxymethyloxy)methyl-N-methoxymethyl-9H-pyrido[3,4-b]indole 
• 304435-42-5 3-(methoxymethyloxy)methyl-N-methoxymethyl-1-trifluoromethanesulfonyloxy-9H-pyrido[3,4-b]indole 
• 1443051-70-4 (R)-(1-(2,2-dimethyl-1,3-dioxolan-4-yl)-9H-pyrido[3,4-b]indol-3-yl)methanol 
• 1443051-69-1 methyl (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-9H-pyrido[3,4-b]indole-3-carboxylate 

Relevant articles and documents

Total syntheses of β-carboline alkaloids, (R)-(-)-pyridindolol K1, (R)-(-)-pyridindolol K2, and (R)-(-)-pyridindolol

The total syntheses of β-carboline alkaloids, (R)-(-)-pyridindolols (1, 5, and 6) are described. The two key steps involved are (1) a thermal electrocyclic reaction of the 3-alkenylindole-2-aldoxime 10 and (2) a thermal cyclization of 3-alkynylindole-2-aldoxime 11 to construct the β-carboline N-oxides 8, which upon heating with acetic anhydride and sequential treatment with trifluoromethanesulfonic anhydride gave the triflates 18. The Stille coupling reaction of 18 with vinylstannane, followed by cleavage of MOM ether, afforded the 1-ethenyl-3-hydroxymethyl-β-carboline (7a). Subsequent acetylation of 7a yielded the acetate 7b, which was subjected to the Sharpless asymmetric 1,2-dihydroxylation by AD-mix-β to produce (R)-(-)-pyridindolol K2 (6). Selective acetylation of 6 was effected by Ac2O and collidine to form (R)-(-)-pyridindolol K1 (5). By contrast, hydrolysis of 6 provided (R)-(-)-pyridindolol (1).

Novel asymmetric total syntheses of (R)-(-)-pyridindolol, (R)-(-)-pyridindolol K1, and (R)-(-)-pyridindolol K2 via a mild one-pot aromatization of N-tosyl-tetrahydro-β-carboline with (S)-2,3-O- isopropylidene-l-glyceraldehyde as the source of chirality

Novel total syntheses of (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 are described. By using l-tryptophan methyl ester and (S)-2,3-O-isopropylidene-l-glyceraldehyde as the starting materials, (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 were synthesized in 5-7 steps in 66%, 41%, and 55% overall yields, respectively. The characteristic step of the total syntheses is a mild one-pot aromatization of N-tosyl-1,2,3,4-tetrahydro-β-carboline (N-Ts-THBC), which was obtained via Pictet-Spengler reaction of l-tryptophan methyl ester with (S)-2,3-O-isopropylidene-l-glyceraldehyde, and subsequent N-tosylation.