204327-16-2

Basic information

• Product Name: 2-Azabicyclo[2.2.1]heptane-3-methanol, (1S,3R,4R)-
• CAS NO: 204327-16-2
• Molecular Formula: C7H13NO
• Molecular Weight: 127.186
• Mol File: 204327-16-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Azabicyclo[2.2.1]heptane-3-methanol, (1S,3R,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azabicyclo[2.2.1]heptane-3-methanol, (1S,3R,4R)-(204327-16-2)
• EPA Substance Registry System: 2-Azabicyclo[2.2.1]heptane-3-methanol, (1S,3R,4R)-(204327-16-2)

Safety Data

• Hazardous Substances Data: 204327-16-2(Hazardous Substances Data)

Upstream product

• 204327-17-3 (1S,3R,4R)-2-aza-bicyclo<2.2.1>heptane-3-carboxylic acid ethyl ester 
• 223505-12-2 (1R,3R,4S)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.1>hept-5-ene-3-carboxylic acid ethyl ester 
• 499137-87-0 (1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carbaldehyde 
• 542-92-7 cyclopenta-1,3-diene 
• 215674-16-1 (1S,3R,4R)-2-[(S)-1-phenylethyl]-3-hydroxymethyl-2-azabicyclo[2.2.1]heptane 
• 166735-47-3 (1R,3R,4S)-2-Aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester 

Downstream Products

• 770737-92-3 (1S,3R,4R)-3-[(diphenylphosphanyl)-methyl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 553645-76-4 (1S,3R,4R)-3-(toluene-4-sulfonyloxymethyl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

(1S, 3R, 4R)-2-azanorbornyl-3-methanol oxazaborolidines in the asymmetric reduction of ketones

Synthesis of new rigid (1S, 3R, 4R)-2-azanorbornyl-3-methanols and its application in the asymmetric borane reduction of ketones are described. The influence of temperature, solvent and concentration on the reation outcome were also studied and enantiomeric excess up to 89% could be obtained.

2-Azanorbornyl alcohols: Very efficient ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones

2-Azanorbornyl-derived amino alcohols were prepared and evaluated as ligands in the Ru(II)-catalyzed asymmetric transfer hydrogenation of aromatic ketones. To improve selectivity and rate, the structure of the ligand was optimized. Acetophenone was reduced using 0.5 mol% catalyst in 40 min in 94% ee. This system was also able to reduce a wide range of aromatic ketones to the corresponding alcohols, while maintaining high enantioselectivities and yields. The effects of catalyst loading and the presence of cosolvents in the reaction vessel were examined, and a linearity study was also done.