2402-83-7Relevant articles and documents
Synthesis and Properties of 2-Oxa-6-azaspiro[3.3]heptane Sulfonate Salts
Van Der Haas, Richard N. S.,Dekker, Jeroen A.,Hassfeld, Jorma,Hager, Anastasia,Fey, Peter,Rubenbauer, Philipp,Damen, Eric
, p. 2394 - 2401 (2017/05/22)
An improved synthesis of the bicyclic spiro compound 2-oxa-6-azaspiro[3.3]heptane is presented. While this compound is often isolated as an oxalate salt, its isolation as a sulfonic acid salt yields a more stable and more soluble product. With these improved properties access to a wider range of reaction conditions with the spirobicyclic 2-oxa-6-azaspiro[3.3]heptane has been enabled.
The Development of a Manufacturing Route to an MCHr1 Antagonist
Golden, Michael,Legg, Danny,Milne, David,Arun Bharadwaj,Deepthi,Gopal, Madan,Dokka, Nagaraju,Nambiar, Sudhir,Ramachandra, Puranik,Santhosh,Sharma, Parhalad,Sridharan,Sulur, Manjunatha,Linderberg, Mats,Nilsson, Anders,Sohlberg, Roger,Kremers, John,Oliver, Samuel,Patra, Debasis
, p. 675 - 682 (2016/04/01)
Process development work to provide an efficient manufacturing route to a MCHr1 antagonist is presented herewith. Features of this development work include a scalable manufacturing route to the useful 6-oxa-2-azaspiro[3.3]heptane building block and the use of a (soluble) alternative to sodium triacetoxyborohydride.
Chemical transformation of 3-bromo-2,2-bis(bromomethyl)-propanol under basic conditions
Ezra, Shai,Feinstein, Shimon,Bilkis, Itzhak,Adar, Eilon,Ganor, Jiwchar
, p. 505 - 512 (2007/10/03)
The mechanism of the spontaneous decomposition of 3-bromo-2,2- bis(bromomethyl)propanol (TBNPA) and the kinetics of the reaction of the parent compound and two subsequent products were determined in aqueous solution at temperatures from 30 to 70 °C and pH from 7.0 to 9.5. TBNPA is decomposed by a sequence of reactions that form 3,3-bis(bromomethyl)oxetane (BBMO), 3-bromomethyl-3-hydroxymethyloxetane (BMHMO), and 2,6-dioxaspiro[3.3]-heptane (DOH), releasing one bromide ion at each stage. The pseudo-first-order rate constant of the decomposition of TBNPA increases linearly with the pH. The apparent activation energy of this transformation (98 ± 2 KJ/mol) was calculated from the change of the effective second-order rate constant with temperature. The pseudoactivation energies of BBMO and BMHMO were estimated to be 109 and 151 KJ/mol, respectively. Good agreement was found between the rate coefficients derived from changes in the organic molecules concentrations and those determined from the changes in the Br- concentrations. TBNPA is the most abundant semivolatile organic pollutant in the aquitard studied, and together with its byproducts they posess an environmental hazard. TBNPA half-life is estimated to be about 100 years. This implies that high concentrations of TBNPA will persist in the aquifer long after the elimination of all its sources.