646530-82-7

Basic information

• Product Name: 2,5-Methano-2H-furo[3,2-b]pyrrol-6-ol, hexahydro-4-methyl-, (2R,3aS,5R,6R,6aR)-rel-(-)- (9CI)
• Synonyms: 2,5-Methano-2H-furo[3,2-b]pyrrol-6-ol, hexahydro-4-methyl-, (2R,3aS,5R,6R,6aR)-rel-(-)- (9CI)
• CAS NO: 646530-82-7
• Molecular Formula: C8H13NO2
• Molecular Weight: 155.19432
• Product Categories: AMINETERTIARY;ALCOHOL
• Mol File: 646530-82-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,5-Methano-2H-furo[3,2-b]pyrrol-6-ol, hexahydro-4-methyl-, (2R,3aS,5R,6R,6aR)-rel-(-)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Methano-2H-furo[3,2-b]pyrrol-6-ol, hexahydro-4-methyl-, (2R,3aS,5R,6R,6aR)-rel-(-)- (9CI)(646530-82-7)
• EPA Substance Registry System: 2,5-Methano-2H-furo[3,2-b]pyrrol-6-ol, hexahydro-4-methyl-, (2R,3aS,5R,6R,6aR)-rel-(-)- (9CI)(646530-82-7)

Safety Data

• Hazardous Substances Data: 646530-82-7(Hazardous Substances Data)

Usage

Molecular weight

193.27 g/mol

Structure

A hexahydro derivative of 4-methyl-2,5-methanofuran with a specific stereochemistry

Stereochemistry

(2R,3aS,5R,6R,6aR)-rel-(-)form

Applications

Potential applications in pharmaceuticals, organic synthesis, and chemical research

Importance

Its specific stereochemistry makes it important in the study of chiral molecules and their interactions with biological systems.

Upstream product

• 26447-85-8 hydroxy-di-thiophen-2-yl-acetic acid methyl ester 
• 498-45-3 scopine 
• 51-34-3 scopolamine 
• 53416-89-0 methyl 3-oxo-8-azabicyclo<3.2.1>oct-6-ene-8-carboxylate 
• 4277-63-8 methyl 1H-pyrrole-1-carboxylate 
• 141938-52-5 (1RS,5SR,6SR,7RS)-methyl 3-oxo-6,7-epoxy-8-azabicyclo[3.2.1]octane-8-carboxylate 
• 109616-30-0 (+/-)-6endo,7exo-diacetoxy-tropane-3endo-ol 
• 105-58-8 Diethyl carbonate 
• 531-44-2 (+/-)-Scopolin 
• 109940-66-1 6exo,7exo-carbonyldioxy-tropan-3-one 
• 7647-01-0 hydrogenchloride 
• 7782-99-2 sulphurous acid 
• 22468-66-2 (+/-)-3endo,7endo-epoxy-8-oxy-tropane-6exo-ol 
• 6820-79-7 9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl-3'-(acetyloxy)-2'-phenyl propanoate 

Downstream Products

• 645417-42-1 (-)-O-acetylscopoline 
• 645417-42-1 (+)-O-acetylscopoline 
• 109451-65-2 (+/-)-6exo-acetoxy-3endo,7endo-epoxy-tropane 
• 109785-40-2 cinnamic acid-(3,7-epoxy-tropan-6-yl ester) 

Relevant articles and documents

A METHOD OF PREPARING THE SCOPINE ESTER OF DI-(2-THIENYL)GLYCOLIC ACID, AN INTERMEDIATE IN THE SYNTHESIS OF TIOTROPIUM BROMIDE

The present invention relates to a preparation method of tiotropium bromide of formula II, comprising the following steps: a) preparation of the scopine ester of formula I by transesterification of methyl di(2thienyl)glycolate of formula IV with scopine of formula III in the presence of a substoichiometric amount of a sterically hindered base selected from the group of alkali salts of branched C3 to C5 alkoxides in an inert solvent, b) isolation of the scopine ester of formula I, and c) quaternization of the scopine ester of formula I with methyl bromide.

Enzymatic Resolution of Tropinone Derivatives

The lipase-mediated kinetic resolution of racemic scopoline [(±)-4] and 6-hydroxytropinone [(±)-7] is reported. Whereas (±)-4 is difficult to resolve due to steric hindrance of the hydroxy function, the resolution of (±)-7 with vinyl acetate as acyl donor gave alcohol (+)-7 and the corresponding acetate (-)-9 with high enantiomeric excess. In case of the optimal result of 99% ee for (+)-7 and 80% ee for (-)-9, an E-value of 35 was calculated. The preparative lipase-catalyzed resolution of (±)-7 resulted in almost enantiopure alcohol (+)-7 with >99% ee after one recrystallization.