930278-38-9

Basic information

• Product Name: (S)-1-(tert-butoxycarbonyl)-4-(4-fluorophenylhydroxymethyl)piperidine
• Synonyms: (S)-1-(tert-butoxycarbonyl)-4-(4-fluorophenylhydroxymethyl)piperidine
• CAS NO: 930278-38-9
• Molecular Weight: 309.381
• Mol File: 930278-38-9.mol

Chemical Properties

• CAS DataBase Reference: (S)-1-(tert-butoxycarbonyl)-4-(4-fluorophenylhydroxymethyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(tert-butoxycarbonyl)-4-(4-fluorophenylhydroxymethyl)piperidine(930278-38-9)
• EPA Substance Registry System: (S)-1-(tert-butoxycarbonyl)-4-(4-fluorophenylhydroxymethyl)piperidine(930278-38-9)

Safety Data

• Hazardous Substances Data: 930278-38-9(Hazardous Substances Data)

Upstream product

• 160296-40-2 tert-butyl 1-[4-(4-fluorobenzoyl)piperidin-1-yl]carboxylate 

Relevant articles and documents

General asymmetric hydrogenation of α-branched aromatic ketones catalyzed by TolBINAP/DMAPEN-ruthenium(II) complex

(Chemical Equation Presented) A catalyst system consisting of RuCl 2[(S)-tolbinap][(R)-dmapen] and t-C4H9OK in 2-propanol effects asymmetric hydrogenation of arylglyoxal dialkylacetals to give the α-hydroxy acetals in up to 98% ee. Hydrogenation of racemic α-amidopropiophenones under dynamic kinetic resolution predominantly gives the syn alcohols in up to 99% ee and >98% de, while the reaction of racemic bezoin methyl ether gives the anti alcohols in excellent stereoselectivity.

Asymmetric hydrogenation of aromatic ketones catalyzed by the TolBINAP/DMAPEN-ruthenium(II) complex: A significant effect of N-substituents of chiral 1,2-diamine ligands on enantioselectivity

(Chemical Equation Presented) Asymmetric hydrogenation of acetophenone in the presence of Ru(II) catalysts coordinated by TolBINAP and a series of chiral 1,2-diamines was studied. The sense and degree of enantioselectivity were highly dependent on the N-substituents of the diamine ligands. The N-substituent effect was discussed in detail. Among these catalysts, the (S)-TolBINAP/(R)- DMAPEN-Ru(II) complex showed the highest enantioselectivity. The mode of enantioface selection was interpreted by using transition state models based on the X-ray structure of the catalyst precursor. The chiral catalyst effected the hydrogenation of alkyl aryl ketones and arylglyoxal dialkyl acetals to afford the chiral alcohol in >99% ee in the best cases. Hydrogenation of racemic benzoin methyl ether with the chiral catalyst through dynamic kinetic resolution gave the anti-alcohol (syn:anti = 3:97) in 98% ee, while the reaction of α-amidopropiophenones resulted in the syn-alcohols (symanti = 96:4 to >99:1) in >98% ee.