91658-09-2

Basic information

• Product Name: (1-Butyl-pentylidene)-((R)-2-methoxymethyl-pyrrolidin-1-yl)-amine
• Synonyms: (1-Butyl-pentylidene)-((R)-2-methoxymethyl-pyrrolidin-1-yl)-amine
• CAS NO: 91658-09-2
• Molecular Weight: 254.416
• Mol File: 91658-09-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1-Butyl-pentylidene)-((R)-2-methoxymethyl-pyrrolidin-1-yl)-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Butyl-pentylidene)-((R)-2-methoxymethyl-pyrrolidin-1-yl)-amine(91658-09-2)
• EPA Substance Registry System: (1-Butyl-pentylidene)-((R)-2-methoxymethyl-pyrrolidin-1-yl)-amine(91658-09-2)

Safety Data

• Hazardous Substances Data: 91658-09-2(Hazardous Substances Data)

Upstream product

• 502-56-7 nonanone-5 
• 72748-99-3 (R)-1-Amino-2-(methoxymethyl)pyrrolidine 
• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 

Downstream Products

• 108439-30-1 (3S,4S)-5-[(E)-(S)-2-Methoxymethyl-pyrrolidin-1-ylimino]-3-phenyl-4-propyl-nonanoic acid methyl ester 
• 502-56-7 nonanone-5 
• 108439-24-3 (3S,4S)-5-Oxo-3-phenyl-4-propyl-nonanoic acid methyl ester 

Relevant articles and documents

Regio-, Diastereo-, and Enantioselective Synthesis of vic-Diols via α-Silyl Ketones According to the SAMP/RAMP Hydrazone Method

α-Silylated ketones 5 or 10 of high enantiomeric purity (ee>=90percent) are easily available by silylation or silylation/alkylation of ketones 1 or 6, resp., according to the SAMP/RAMP hydrazone method.Reduction of 5 or 10 with L-selectride, followed by oxidative cleavage of the C-Si bond, leads to vic-diols 11-13 with high diastereoselectivity (de>=90percent) and without racemization.The stereoselectivity of the reduction depends on the structure of the α-silyl ketones 5 or 10, the reducing reagents, and the solvents used.Key Words: Ketones, α-silyl / vic-Diols, diastereo- and enantioselective synthesis / SAMP/RAMP Hydrazones / L-Selectride reductions

ASYMMETRIC SYNTHESES VIA METALATED CHIRAL HYDRAZONESOVERALL ENANTIOSELECTIVE α-ALKYLATION OF ACYCLIC KETONES

A general method is described, which allows the overall enantioselective α-alkylation of acyclic ketones in good overall yields (44-86percent, 4 steps) and enantioselectivities ranging routinely from >94percent ee up to virtually complete asymmetric induction (99.5percent ee).The acyclic ketones are transformed to their corresponding "SAMP-hydrazones" (S)-2 by reaction with the enantiomerically pure hydrazine (S)-1-amino-2-methoxymethyl-pyrrolidine , readily available from (S)-proline.Metalation to form chiral azaenolates (S)-3 of ECCZCN-configuration and then alkylation to product hydrazones 4, followed by hydrazone cleavage via acidic hydrolysis of methiodides 9 in a two phase system or ozonolysis, leads to α-substituted, enantiomerically enriched, acyclic ketones 5.In special cases, where a phenyl group is directly attached to the newly generated center of chirality (5n,o,p), only low enantiomeric excesses are observed. 17 Examples, including first applications in natural product synthesis (cf 5a,b,e, and h) are summarized.