69498-25-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-Methylpyrrolidine is used as a reactant for the preparation of benzazepineylidene acetamide derivatives. These derivatives serve as arginine vasopressin V2 receptor agonists, which have potential applications in the development of drugs targeting the arginine vasopressin system. This system plays a crucial role in regulating water balance in the body, and modulation of the V2 receptor can have therapeutic effects in conditions such as diabetes insipidus and potentially other water balance disorders.

InChI:InChI=1/C5H11N/c1-5-2-3-6-4-5/h5-6H,2-4H2,1H3/t5-/m0/s1

Upstream product

• 235094-13-0 1-((2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-phenylselanylmethyl-hexahydro-benzo[e][1,3]oxazin-3-yl)-propenone 
• 186597-27-3 (2S,3aS,4aR,6R,8aS)-2,6,9,9-Tetramethyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one 
• 155627-27-3 (3S,6S,7aR)-6-Methyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 186597-31-9 (3'S)-8-(3'-methylpyrrolidinyl)menthol 

Relevant academic research and scientific papers

Diastereoselective 5-exo-trig radical cyclisation on N-acryloyl-tetrahydro-1,3-oxazines. A novel approach to enantiopure 3-substituted pyrrolidines

N-acryloyl-2-(phenylselenomethyl)-tetrahydro-1,3-oxazine 1 generates a carbon-centred radical in the presence of tri-n-butyltin hydride and AIBN. This radical underwent diastereoselective 5-exo-trig cyclisation leading to a mixture of five-membered lactams 2a and 2b (d.e. 68%). Chromatographic separation of the diastereomers and elimination of the chiral auxiliary provided enantiopure (R)-3-methylpyrrolidine in good chemical yield. Copyright (C) 1996 Elsevier Science Ltd.

A synthesis of enantiomerically pure 3- and 3,3-disubstituted pyrrolidines

Enantiomerically pure bicyclic lactam 1, derived from (S)-phenylglycinol, underwent diastereoselective mono- and dialkylation affording substituted lactams 2 and 3 bearing tertiary and quaternary stereocenters. Reduction with LiAlH4 furnished N