157810-21-4

Basic information

• Product Name: (1R,4S)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one
• Synonyms: (1R,4S)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one
• CAS NO: 157810-21-4
• Molecular Weight: 139.154
• Mol File: 157810-21-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,4S)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one(157810-21-4)
• EPA Substance Registry System: (1R,4S)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one(157810-21-4)

Safety Data

• Hazardous Substances Data: 157810-21-4(Hazardous Substances Data)

Upstream product

• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 

Downstream Products

• 138923-03-2 (1S,4R)-(-)-methyl-4-aminocyclopent-2-en-1-carboxylate hydrochloride 
• 102579-71-5 (-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 

Relevant articles and documents

Enhanced enzymatic synthesis of the enantiopure intermediate for the blockbuster drug intermediate abacavir through a two-step enzymatic cascade reaction

A very efficient enzymatic two-step cascade reaction was devised (E?>?200) for the resolution of activated γ-lactams (±)-1 and (±)-2. The N-hydroxymethyl group worked as a traceless activating group, when the reactions were performed with H2O (0.5?equiv) in the presence of benzylamine (1?equiv) in i-Pr2O at 60?°C. The ring-opened enantiomerically pure γ-amino acids (1S,4R)-6 (ee?=?99%, intermediate of abacavir) and (1S,3R)-8 (ee?=?99%) and unreacted lactams (1S,4R)-1 and (1R,4S)-2 (ee???96%) were obtained in good yields (?43%). Treatment of (1S,4R)-1 and (1R,4S)-2 with 18% HCl or NH4OH resulted in (1R,4S)-6·HCl and (1S,3R)-8·HCl or (1S,4R)-3 and (1R,4S)-4 quantitatively, with ee???96%.