177082-91-6

Basic information

• Product Name: (R)-(+)-2-Methoxymethyl-pyrrolidin-1-dithiocarbonsaeure-benzyl-ester
• Synonyms: (R)-(+)-2-Methoxymethyl-pyrrolidin-1-dithiocarbonsaeure-benzyl-ester
• CAS NO: 177082-91-6
• Molecular Weight: 281.443
• Mol File: 177082-91-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-(+)-2-Methoxymethyl-pyrrolidin-1-dithiocarbonsaeure-benzyl-ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2-Methoxymethyl-pyrrolidin-1-dithiocarbonsaeure-benzyl-ester(177082-91-6)
• EPA Substance Registry System: (R)-(+)-2-Methoxymethyl-pyrrolidin-1-dithiocarbonsaeure-benzyl-ester(177082-91-6)

Safety Data

• Hazardous Substances Data: 177082-91-6(Hazardous Substances Data)

Upstream product

• 75-15-0 carbon disulfide 
• 100-39-0 benzyl bromide 
• 63126-47-6 (2R)-methoxymethylpyrrolidine 

Relevant articles and documents

Synthesis and reactions of chiral dithiocarbamates derived from (R)-(-)- or (S)-(+)-2-

The synthesis, diastereoselective alkylation reactions, dithiocarboxylation, and aldol condensation of several substituted methyl (R1-CH2) (S)-2-(methoxymethyl)-pyrrolidine-1-dithiocarboxylates (S)-2 and of the corresponding (R)-derivatives (R)-2 are described. The new enantiomeric dithiocarbamates (S)-2a-e, and (R)-2a-d are obtained by reaction of (S)-(+)- [(S)-1] or (R)-(-)-2-(methoxymethyl)-pyrrolidine [(R)-1], respectively, with carbon disulfide in dry methanol/anhydrous sodium acetate and the appropriate alkylating agent. The cyclic ketene dithioacetals (S)-3 and (R)-3 are formed by dithiocarboxylation procedure of (S)-2a and (R)-2a whereas (S)-6 and (R)-6 are obtained by aldol reaction with isobutyraldehyde. (S)-2c,d and (R)-2c,d react in a diastereoselective manner after deprotonation with n-BuLi or LiTMP/LiBr at -78°C in THF with alkyl halides to the enantiomeric compounds 4a/ent-4a, 4b/ent-4b and 5/ent-5, respectively. Johann Ambrosius Barth 1996.