89876-71-1

Basic information

• Product Name: (2S,1'S)-N,3-dimethyl-N'-1'-phenylpropyl-2-hydrazinobutanol
• Synonyms: (2S,1'S)-N,3-dimethyl-N'-1'-phenylpropyl-2-hydrazinobutanol
• CAS NO: 89876-71-1
• Molecular Weight: 250.384
• Mol File: 89876-71-1.mol

Chemical Properties

• CAS DataBase Reference: (2S,1'S)-N,3-dimethyl-N'-1'-phenylpropyl-2-hydrazinobutanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,1'S)-N,3-dimethyl-N'-1'-phenylpropyl-2-hydrazinobutanol(89876-71-1)
• EPA Substance Registry System: (2S,1'S)-N,3-dimethyl-N'-1'-phenylpropyl-2-hydrazinobutanol(89876-71-1)

Safety Data

• Hazardous Substances Data: 89876-71-1(Hazardous Substances Data)

Upstream product

• 89876-67-5 (S)-N,3-dimethyl-N-nitroso-2-aminobutanol 
• 89876-68-6 (S)-N,3-dimethyl-2-hydrazinobutanol 
• 89876-66-4 (S)-N-[1-(hydroxymethyl)-2-methylpropyl]formamide 
• 78617-54-6 (s)-N-methylvalinol 
• 2026-48-4 (S)-valinol 
• 89876-69-7 (E)-(S)-N'-benzylidene-N,3-dimethyl-2-hydrazinobutanol 

Downstream Products

• 3789-59-1 (R)-1-phenylpropylamine 
• 78617-54-6 (s)-N-methylvalinol 

Relevant articles and documents

Alkylation of a Chiral Hydrazone by Means of Asymmetric Addition of Grignard Reagents to the Carbon-Nitrogen Double Bond

A chiral hydrazone, (E)-(S)-N'-benzylidene-N,3-dimethyl-2-hydrazinobutanol (6), was synthesized from (S)-valinol.Compound was reacted with Grignard reagents to give optically pure (2S,1'S)-N,3-dimethyl-N'-1'-phenylalkyl-2-hydrazinobutanols (7a and 7b).However, N'-2-aryl-1'-phenylethyl-N,3-dimethyl-2-hydrazinobutanols (7c and 7d) were each obtained as a mixture of two diastereomers.Nitrogen-nitrogen bonds of 7a and 7b were cleaved by hydrogenolysis to give (S)-1-phenylalkyamines (8a and 8b), and their absolute configurations and optical purities were confirmed.These reactions were assumed to proceed via the chelated six-membered ring intermediates.Keywords -- absolute configuration; asymmetric reaction; chelated intermediate; chiral hydrazine; chiral hydrazone; conformation control; l-ephedrine; Grignard reaction; stereoselectivity; (S)-valinol