220926-88-5

Basic information

• Product Name: N-(tert-butoxycarbonyl)-N-(4-chlorobutyl)cinnamylamine
• Synonyms: N-(tert-butoxycarbonyl)-N-(4-chlorobutyl)cinnamylamine
• CAS NO: 220926-88-5
• Molecular Weight: 323.863
• Mol File: 220926-88-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(tert-butoxycarbonyl)-N-(4-chlorobutyl)cinnamylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-butoxycarbonyl)-N-(4-chlorobutyl)cinnamylamine(220926-88-5)
• EPA Substance Registry System: N-(tert-butoxycarbonyl)-N-(4-chlorobutyl)cinnamylamine(220926-88-5)

Safety Data

• Hazardous Substances Data: 220926-88-5(Hazardous Substances Data)

Upstream product

• 4392-24-9 Cinnamyl bromide 
• 17480-07-8 2-[(E)-3-phenylprop-2-enyl]-2,3-dihydro-1H-isoindole-1,3-dione 
• 6940-78-9 4-chlorobutyl bromide 
• 115270-11-6 tert-butyl N-[(2E)-3-phenylprop-2-en-1-yl]carbamate 

Downstream Products

• 26250-84-0 (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid 
• 220926-89-6 (S)-2-[(E)-styryl]piperidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Asymmetric syntheses of N-Boc 2-substituted pyrrolidines and piperidines by intramolecular cyclization

Asymmetric lithiation-substitutions by n-BuLi/(-)-sparteine with the N- Boc-N-(3-halopropyl)allylamines 1-4 provide the N-Boc-2-alkenylpyrrolidines (S)-5, (S)-6, and (S)-7 in yields of 3193% with enantiomeric ratios (ers) from 65:35 to 90:10. These reactions are shown to involve an initial asymmetric deprotonation, but the enantiodetermining step is a subsequent asymmetric cyclization under the influence of the chiral ligand. Extension to formation of a piperidine is illustrated by reaction of N-Boc-(4- chlorobutyl)cinnamylamine (9) to afford (S)-N-Boc-2-(trans-β- styryl)piperidine ((S)-10) in 68% yield with an enantiomeric ratio (er) of 84:16. Analogous reactions with epoxide ring openings of N-Boc-N- (oxaalkenyl)benzylamines 11 and 12 afford the corresponding N-Boc-2-phenyl- 3-(hydroxymethyl)pyrrolidine (13) in 67% yield with a diastereomeric ratio (dr) of 50:50 and ers of 97:3 and 95:5 and the corresponding N-Boc-2-phenyl- 3-(hydroxymethyl)piperidine (14) in 29% yield with a dr of 86:14 and ers of 81:19 and 86:14.