214678-96-3

Basic information

• Product Name: (1R,2S,1'S)-(+)-N-<1-methyl-2-(2'-methyl-1'-nitromethylpropoxy)-2-phenylethyl>formamide
• Synonyms: (1R,2S,1'S)-(+)-N-<1-methyl-2-(2'-methyl-1'-nitromethylpropoxy)-2-phenylethyl>formamide
• CAS NO: 214678-96-3
• Molecular Weight: 294.351
• Mol File: 214678-96-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,2S,1'S)-(+)-N-<1-methyl-2-(2'-methyl-1'-nitromethylpropoxy)-2-phenylethyl>formamide(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,1'S)-(+)-N-<1-methyl-2-(2'-methyl-1'-nitromethylpropoxy)-2-phenylethyl>formamide(214678-96-3)
• EPA Substance Registry System: (1R,2S,1'S)-(+)-N-<1-methyl-2-(2'-methyl-1'-nitromethylpropoxy)-2-phenylethyl>formamide(214678-96-3)

Safety Data

• Hazardous Substances Data: 214678-96-3(Hazardous Substances Data)

Upstream product

• 141377-55-1 3-methyl-1-nitrobutan-2-ol 
• 27675-38-3 (E)-3-methyl-1-nitro-but-1-ene 
• 81626-21-3 (1S,2R)-2-formamido-1-phenylpropanol 

Downstream Products

• 214679-11-5 (1R,2S,1'S)-(+)-N-<2-(1'-tert-butoxycarbonylaminomethyl-2'-methylpropoxy)-1-methyl-2-phenylethyl>formamide 
• 185426-14-6 (2S)-(+)-1-tert-butoxycarbonylamino-3-methylbutan-2-ol 

Relevant articles and documents

Diastereo- and enantioselective synthesis of vicinal amino alcohols by oxa Michael addition of N-formylnorephedrine to nitro alkenes

The first intermolecular asymmetric oxa Michael additions with removable chirality information within the hydroxide source are reported. As enantiopure oxygen nucleophile functioning as chiral hydroxide equivalent N-formylnorephedrine (7) was used and conjugate additions to aliphatic (E)-nitro alkenes 2a-j were carned out in good yields (35-87%) and excellent diastereomeric excesses (de = 94-≥98%). After reduction of the nitro group and protection of the amino function (11a-h, 73-87%, both steps), the cleavage of the auxiliary occurred without epimerisation (69-99%) using Na/NH3. The Boc-protected 2-amino alcohols 12a-h could be obtained in good overall yields (30-58 %, four steps) and excellent diastereomeric and enantiomeric excesses (de, ee = 94-≥98%). Transition states explaining the overall stereochemical outcome are presented based on the absolute configuration determined by X-ray structure analysis on 8b.