1228099-85-1

Basic information

• Product Name: (S)-2-[1'-(cyclohexylmethyl)-3,4-dihydrospiro[[2]benzopyran-1,4'-piperidin]-3-yl]ethanol
• Synonyms: (S)-2-[1'-(cyclohexylmethyl)-3,4-dihydrospiro[[2]benzopyran-1,4'-piperidin]-3-yl]ethanol
• CAS NO: 1228099-85-1
• Molecular Weight: 343.51
• Mol File: 1228099-85-1.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-[1'-(cyclohexylmethyl)-3,4-dihydrospiro[[2]benzopyran-1,4'-piperidin]-3-yl]ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-[1'-(cyclohexylmethyl)-3,4-dihydrospiro[[2]benzopyran-1,4'-piperidin]-3-yl]ethanol(1228099-85-1)
• EPA Substance Registry System: (S)-2-[1'-(cyclohexylmethyl)-3,4-dihydrospiro[[2]benzopyran-1,4'-piperidin]-3-yl]ethanol(1228099-85-1)

Safety Data

• Hazardous Substances Data: 1228099-85-1(Hazardous Substances Data)

Upstream product

• 76360-25-3 1-(4,4-dimethoxypiperidin-1-yl)ethan-1-one 
• 2550-36-9 Cyclohexylmethyl bromide 

Relevant articles and documents

Lipase-catalyzed kinetic resolution as key step in the synthesis of enantiomerically pure σ ligands with 2-benzopyran structure

In order to obtain enantiomerically pure σ1 receptor ligands with a 2-benzopyran scaffold an Oxa-Pictet-Spengler reaction with the enantiomerically pure 2-phenylethanol derivatives (R)-4 and (S)-4 was envisaged. The kinetic resolution of racemic alcohol (±)-4 using Amano Lipase PS-C II and isopropenyl acetate in tert-butyl methyl ether led to the (R)-configured alcohol (R)-4 in 42% yield with an enantiomeric excess of 99.6%. The (S)-configured alcohol (S)-4 was obtained by Amano Lipase PS-C II catalyzed hydrolysis of enantiomerically enriched acetate (S)-5 (76.9% ee) and provided (S)-4 in 26% yield and 99.7% ee. The absolute configuration of alcohol (R)-4 was determined by exciton coupled CD spectroscopy of the bis(bromobenzoate) (R)-7. The next important step for the synthesis of 2-benzopyrans 2 and 3 was the Oxa-Pictet-Spengler reaction of the enantiomerically pure alcohols (R)-4 and (S)-4 with piperidone ketal 8 and chloropropionaldehyde acetal 12. The conformationally restricted spirocyclic 2-benzopyrans 2 revealed higher σ1 affinity than the more flexible aminoethyl derivatives 3. The (R)- and (R,R)-configured enantiomers (R)-2 and (R,R)-3 represent the eutomers of this class of compounds with eudismic ratios of 4.8 (2b) and 4.5 (2c). High σ1/σ2 selectivity (>49) was found for the most potent σ1 ligands (R)-2b, (R)-2c, (R)-2d, and (S)-2d (Ki(σ1) 9–15?nM).