69001-12-3

Upstream product

• 67-56-1 methanol 
• 52745-20-7 (2-aminophenyl)(pyrrolidin-1-yl)methanone 
• 3389-54-6 n-benzoylpyrrolidine 
• 118-48-9 isatoic anhydride 
• 5874-58-8 N-(benzoyl)-L-proline 

Downstream Products

• 69001-40-7 N-(4,4-Dimethoxybutyl)benzamid 
• 76290-79-4 INS 48836 
• 68471-55-6 (2,3-dihydro-1H-pyrrol-1-yl)(phenyl)methanone 
• 4753-09-7 N-benzoyltryptamine 
• 73269-78-0 N-benzoyl-2-(5-fluorouracil-1-yl)pyrrolidine 
• 96133-48-1 (2-hydroxypyrrolidin-1-yl) (phenyl)methanone 

Relevant academic research and scientific papers

Memory of Chirality in Flow Electrochemistry: Fast Optimisation with DoE and Online 2D-HPLC

Amino acid derivatives undergo non-Kolbe electrolysis to afford enantiomerically enriched α-alkoxyamino derivatives through intermediate chiral carbenium ions. The products contain N,O-acetals which are important structural motifs found in bioactive natural products. The reaction is performed in a continuous flow electrochemical reactor coupled to a 2D-HPLC for immediate online analysis. This allowed a fast screening of temperature, electrode material, current, flow-rate and concentration in a DoE approach. The combination with online HPLC demonstrates that also stereoselective reactions can benefit from a hugely accelerated optimisation by combining flow electrochemistry with multidimensional analysis.

Visible-light photocatalytic α-amino C(sp3)–H activation through radical translocation: a novel and metal-free approach to α-alkoxybenzamides

Visible-light photocatalytic, metal-free synthesis of valuable α-alkoxybenzamides starting with readily prepared o-aminobenzamides and alcohols through radical translocation under mild conditions is reported. This protocol employs eosin Y as an organophot

Electrochemical deallylation of α-allyl cyclic amines and synthesis of optically active quaternary cyclic amino acids

Electrochemical oxidation of α-allylated and α-betizylated N-acylated cyclic amines by using a graphite anode easily affords the corresponding α-methoxylated products with up to 76% yield. Ease of oxidation was affected by the type of electrode, the size

Ring contraction of of α,β-unsaturated cyclic amines with cis-dihydroxylation at the α,β-position

α,β-Unsaturated cyclic amines are oxidized by OsO4 to afford α,β-cis-dihydroxylated compounds which are thermodynamically transformed into ring-opened keto-alcohols. The keto-alcohols are then cyclized to form synthetically useful ring-contracted cyclic amines.

Exploratory synthetic studies of the α-methoxylation of amides via cuprous ion-promoted decomposition of o-diazobenzamides

A convenient nonelectrochemical amide oxidation method has been developed. The process involves a cuprous ion-promoted decomposition of o-diazobenzamides like 4, generated in situ from the corresponding o-aminobenzamides, to give N-acyliminium ion intermediate 9 via a 1,5-H-atom transfer, followed by metal-catalyzed oxidation of the resulting α-amidyl radical. The transformation produces α-methoxybenzamides 15 in good yields. An attempt was made to apply this oxidation method to a total synthesis of the alkaloid (-)-anisomycin (16). Scalemic o-aminobenzamide pyrrolidine derivatives 18a/18b underwent oxidation to give α-methoxylated amide substrates 19a/19b, respectively, in good yields. However, alkylation of the N-acyliminium intermediate 20 with (p-methoxybenzyl)magnesium chloride gave the undesired anti-compounds 22a/22b as the major products. The amide oxidation exhibits good regioselectivity with many unsymmetrical 2-substituted piperidine and pyrrolidine systems. In general, it appears that the larger the C-2 substituent, the greater the methylene/methine H-atom abstraction ratio. A mechanistic rationale for this selectivity is suggested based upon amide rotamer populations. An extension of this methodology can be used to conduct two sequential amide oxidations using readily prepared 2-amino-6-nitrobenzamides such as 68 and 69.

A convenient synthetic method for amide oxidation

Diazotization of o-aminobenzamides in methanol in the presence of a catalytic amount of CuCl affords α-methoxybenzamides in good yields.

A Convenient Route to β-Aryl-substituted Cyclic Enamines as Key Synthetic Intermediates of Sceletium and Amaryllidaceae Alkaloids

Aryl groups were introduced into the position β to the nitrogen atom of cyclic amines by carrying out the anodic α-methoxylation of cyclic amine derivatives, the elimination of methanol from the oxidized products, the halomethoxylation of the resulting α,β-unsaturated cyclic amine derivatives, the replacement of the α-methoxy group with an aryl group, and the silver ion-promoted migration of the α-aryl group to the β-position, consecutively.This method was applied to the synthesis of some alkaloids such as (+/-)-mesembrine.

Electroorganic Chemistry. Part 80. α-Hydroxylation of N-Acylated Cyclic Amines and Utilization of the Products as Amino Aldehyde Equivalents

A general method for the transformation of N-acylated cyclic amines (1) to amino aldehydes (4) was exploited.N-Benzoyl- or N-alkoxycarbonyl-α-methoxyamines (2) were prepared by anodic reaction of (1) in methanol.Treatment of (2) with dilute hydrochloric acid gave the corresponding α-hydroxylated compounds (3) which are amino aldehydes equivalents.The reaction of (3) with methoxycarbonylmethylenetriphenylphosphorane yielded ω-amino-α,β-unsaturated esters in satisfactory yields.

A GENERAL METHOD FOR THE SYNTHESIS OF INDOLES BEARING A VARIETY OF SUBSTITUENTS AT THE β-POSITION, AND ITS APPLICATION TO THE SYNTHESIS OF L-TRYPTOPHAN

A general synthetic method of β-substituted indoles such as indolacetic acid, tryptamine and L-tryptophan has been exploited utilizing α-methoxylated amides, lactams, a carbamate, and sulfonamides, easily obtainable by an electrochemical method, as key intemediates.