The Reaction of β-Amino Alcohols with 1,1′-Carbonyldiimidazole − Influence of the Nitrogen Substituent on the Reaction Course

Abstract

The reaction of β‐amino alcohols with 1,1′‐carbonyldiimidazole in dichloromethane is affected by the size of the nitrogen substituent. 1,3‐Oxazolidin‐2‐ones are exclusively obtained from N‐H, N‐methyl and N‐arylmethyl derivatives. O‐(1‐Imidazolyl)carbonyl derivatives are formed as intermediates from N‐[1‐(2‐pyridyl)alkyl]‐(S)‐valinol and are mainly or exclusively converted into aziridines in the presence of water, although the cyclization is impeded by large N‐substituents such as triphenylmethyl.

Expedient synthesis of pseudo-Pro-containing peptides: towards constrained peptidomimetics and foldamers

“…22 Nevertheless, none of the procedures attempted by us gave the oxazolidinone-peptide 2 in a significant yield. The reaction of 1a with 1,1′-carbonyldiimidazole (CDI) and DIPEA 23 gave Ts-Ala-Dha-PheNH 2 (3) as the major product, and only traces of 2a (entry 7), the rest being the reagent. The treatment of 1a with Boc 2 O and DIPEA (entry 8) or DMAP 24 (entry 9) gave a Boc-derivative of 1 (not isolated) and traces of 2, as determined by the HPLC-MS analysis of the reaction mixture.…”

Convenient Method for Synthesis of l-Methamphetamine

“…In the earlier reports 12,13) , the enantiomers of compounds 2 and 3 were prepared from l-NE and l-EP, respectively, under similar conditions as in reaction A, and compound 2 was obtained from d-NE treated with diethylcarbonate and potassium carbonate in good yield (83), whereas there was no report on the synthesis of MA from compound 3. In this study, we have developed a highly e‹cient enantioselective preparation method of l-MA using the commercially available d-NE (1) as the starting material.…”

Oxazolidin-2-one Ring, a Popular Framework in Synthetic Organic Chemistry: Part 1. The Construction of the Oxazolidin-2-one Ring

“…1,3-Oxazolidin-2-ones were also synthesized in good yields from β-aminoalcohols by treatment with 1,1'-carbodiimidazole (CDI) [ Savoia et al investigated [13] the influence of the nitrogen-substituent in the reaction with CDI of Nsubstituted β−aminoalcohols (6): cyclic carbamates 7 are formed exclusively and in high yields from substrates bearing small N-substituents, such as Me or Et, whereas the competitive formation of the aziridines 8 is favoured by large N-substituent, as shown in Scheme 4a.…”