55709-17-6

Upstream product

• 2555-05-7 3-methyl-2-pyrrolidinone 
• 181293-43-6 (3S,2'S)-2'-(1-Ethyl-1-methoxy-propyl)-3-methyl-[1,1']bipyrrolidinyl-2-one 

Downstream Products

• 205808-16-8 (S)-4-[(tert-butoxycarbonyl)amino]-2-methylbutanoic acid 

Relevant academic research and scientific papers

CARBAZOLE-CONTAINING AMIDES, CARBAMATES, AND UREAS AS CRYPTOCHROME MODULATORS

The subject matter herein is directed to carbazole-containing amide, carbamate, and urea derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, D, E, G, J, L, M, Q, a, and b are accordingly described. Also provided are pharmaceutical compositions containing the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, complications associated with diabetes, Cushing's syndrome, NASH, NAFLD, asthma, and COPD.

Separation of (S)-(-)-3-methyl-2-pyrrolidinone as an inclusion complex with (R)-(+)-4,4′,6,6′-tetrachloro-2,2′-bis(hydroxydiphenylmethyl) -1,1′-biphenyl host and its X-ray structural study

By inclusion complexation with the chiral host compound (R)-(+)-4,4′,6,6′-tetrachloro-2,2′-bis(hydroxydiphenylmethyl) -1,1′-biphenyl, racemic 3-methyl-2-pyrrolidinone was resolved and its (S)-(-)-enantiomer was isolated as a 1:1 inclusion complex, which crystallises in the orthorhombic crystal system in the space group P212 121 (a = 14.1163(2) A, b = 14.7140(3) A, c = 17.2025(3) A). By the inclusion complexation, the keto-enol equilibrium of the guest was frozen and the keto-form was isolated in a pure form. By X-ray structural study of the complex, the guest molecule included was elucidated to be the keto-form and its absolute configuration was determined to be (S).

Optical resolution of cyclic amides by inclusion in dehydrocholic acid

Dehydrocholic acid serves as an effective chiral host for the resolution of several five-, six-, and seven-membered cyclic amides by inclusion.

Asymmetric synthesis of 3-substituted pyrrolidones via α-alkylation of a chiral non-racemic γ-lactam

3-Alkyl pyrrolidones 9 were synthesized in good yield and high diastereoselectivity by α-alkylation of the new chiral non-racemic lactam 8 derived from (R)-(-)-phenylglycinol. After debenzylation and introduction of an electron-withdrawing group, 3-methylpyrrolidone 10 is easily hydrolyzed in a basic medium to produce γ-aminobutyric acid (GABA) analogue 13.

Enantioselective synthesis of 2-substituted 5-, 6- and 7-membered lactams via α-alkylation of their chiral N-dialkylamino derivatives

2-Alkyl-substituted lactams 4 were synthesized in good overall yields and high enantiomeric purities (ee = 71-99%) by α-alkylation of chiral N-(dialkylamino)lactams 2 and subsequent reductive N-N bond cleavage of the resulting lactams 3 with lithium in liquid ammonia. The lactams 2, in turn, were prepared in good yields by cyclization of ω-chloroalkanohydrazides 1 with sodium hydride. Acidic hydrolysis of lactams 4 leads to γ-aminobutanoic acid (GABA) derivatives 5 (ee ≤ 99%). The absolute configuration was determined by polarimetry and an X-ray structure analysis of (S,S)-3e'.

Optically Active 4,4',6,6'-Tetrachloro-2,2'-bis(hydroxydiphenylmethyl)biphenyl As a Host for Optical Resolution and Chiral Shift Reagent

The title biphenyl derivative was found to be useful as a host for optical resolution and as a chiral shift reagent for the determination of the optical purity and the absolute configuration of a wide variety of chiral compounds.