63399-77-9

Usage

Uses

Used in Pharmaceutical Industry:
H-ALPHA-ME-D-PRO-OH is used as a building block for the synthesis of various pharmaceutical compounds, such as (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine. It is also used in the formal synthesis of (-)-Lasubine II and (+)-Cermizine C. The presence of this amino acid in the synthesis process contributes to the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
H-ALPHA-ME-D-PRO-OH is used as a key intermediate in the chemical synthesis of various organic compounds. Its unique structure allows for the creation of complex molecules that can be utilized in a wide range of applications, from pharmaceuticals to materials science.

InChI:InChI:1S/C6H11NO2/c1-6(5(8)9)3-2-4-7-6/h7H,2-4H2,1H3,(H,8,9)

Upstream product

• 1415303-35-3 1-(carbamoyl phenylmethyl)-2-cyano-2-methylpyrrolidine 
• 111080-58-1 1-benzyl-2-methylpyrrolidine-2-carboxamide 
• 1310563-79-1 1-benzyl-2-methylpyrrolidine-2-carbonitrile 
• 5891-21-4 5-chloro-2-pentanone 
• 848488-83-5 DL-(α-methyl)proline amide 
• 104739-12-0 (S)-3-Isopropyl-1-methoxy-8a-methyl-6,7,8,8a-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-4-one 

Downstream Products

• 166170-15-6 (R)-1-(tert-butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid 
• 1268520-34-8 1,2-dimethyl-D-proline 
• 1207754-99-1 tert-butyl (R)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate 
• 912444-00-9 veliparib 
• 63399-76-8 (7aR)-7a-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3]oxazole-1,3-dione 
• 1400280-16-1 (2R)-1-(3-chloro-2-methylphenylsulfonyl)-N-(1-hydroxyadamant-3-yl)-2-methylpyrrolidine-2-carboxamide 
• 1422435-02-6 C₁₄H₁₈ClNO₄S 
• 1400280-15-0 (2R)-1-(3-chloro-2-methylphenylsulfonyl)-N-(2-adamantyl)-2-methylpyrrolidine-2-carboxamide 
• 1400280-22-9 (2R)-2-methyl-1-(4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenylsulfonyl)pyrrolidine-2-carboxylic acid 
• 1400280-21-8 (R)-methyl 1-(4-acetylphenylsulfonyl)-2-methylpyrrolidine-2-carboxylate 

Relevant academic research and scientific papers

Α-substd. provitamin optically active production of phosphorus

PROBLEM TO BE SOLVED: To provide an industrial method practically suitable for producing an optically active α-substituted prolines with short process and mild conditions.SOLUTION: A method of producing an optically active α-substituted prolines (6) includes (d) a step of obtaining an optically active N, α-substituted prolines (5) by hydrolysis of an optically active N, α-substituted proline amides (4), and (e) a step of obtaining an optically active α-substituted prolines (6) by eliminating the optically active N, and a protective group Rof the α-substituted prolines (5).

METHOD FOR PRODUCING OPTICALLY ACTIVE ALPHA-SUBSTITUTED PROLINE

The present invention aims to provide an industrial method practically suitable for producing optically active α-substituted prolines from an acyclic ketone compound by a small number of steps under mild conditions. The present invention relates to a production method of an optically active α-substituted proline (4) and/or an optically active α-substituted prolinamide (5), including (a) reacting an acyclic ketone compound (1) with at least one selected from ammonia, an ammonium salt, primary amine and a salt of primary amine, and a cyanating agent to give a cyclic nitrogen-containing compound (2), (b) hydrating the cyclic nitrogen-containing compound (2) to give an α-substituted prolinamide (3), and (c) resolving the α-substituted prolinamide (3) by one or more of (d) enzymatical hydrolysis, (e) resolution by diastereomeric salt formation, and (f) separation by column chromatography.

Is the backbone conformation of Cα-methyl proline restricted to a single region?

Cα-Methyl-L-proline, or L(αMe)Pro, is probably the most conformational constrained α-amino acid. In particular, its ω and o torsion angles are restricted to about 180 and -60°, respectively, and only three ranges of values are theoretically ava