Industrial synthesis of serinol
AssigneeBracco Imaging S.P.A.
InventorsLuciano Lattuada, Giovanni Battista Giovenzana, Camilla Cavallotti, Ivan Menegotto
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Abstract
The present invention is related to the synthesis of 4-hydroxymethyl-2-oxazolidinone (serinol carbamate, SC), which can be subsequently hydrolyzed to 2-amino-1,3-propanediol (serinol), by reacting glycerol and urea: (I) In general, glycerol is heated with urea and a catalyst, with or without a solvent, to give mainly 4-hydroxymethyl-2-oxazolidinone (serinol carbamate, SC), which is hydrolyzed in the next step to 2-amino-1,3-propanediol (serinol). Alternatively, glycerol 1,2-carbonate can be used instead of glycerol. Serinol obtained by the process of the invention may be used in the synthesis of Iopamidol.
Claims20
A process for preparing 2-amino-1,3-propanediol (serinol) of formula (I):
- said process comprising the steps of:
- i) reacting glycerol or glycerol 1,2-carbonate with urea at a temperature higher than or equal to 130° C. in the presence of a catalyst selected from Mg, MgO, Mg(OMe)2, Mg(OH)2 and La2O3, wherein the molar ratio urea/glycerol or urea/glycerol 1,2-carbonate ranges from 1:1 to 4:1, and wherein the ratio catalyst/glycerol or catalyst/glycerol 1,2-carbonate ranges from 0.1:1 to 1:1, to provide selectively 4-hydroxymethyl-2-oxazolidinone (serinol carbamate) of formula (II):
- as the main product over glycerol carbonate and over isoserinol carbamate;
- ii) hydrolyzing the serinol carbamate to obtain serinol;
- and
- iii) optionally converting the serinol into a salt thereof.
A process for preparing 2-amino-1,3-propanediol (serinol) of formula (I):
- said process comprising the steps of:
- i) reacting glycerol or glycerol 1,2-carbonate with urea at a temperature higher than or equal to 130° C. in the presence of a catalyst selected from Mg, MgO, Mg(OMe)2, Mg(OH)2 and La2O3 to provide 4-hydroxymethyl-2-oxazolidinone (serinol carbamate) of formula (II):
- ii) hydrolyzing the serinol carbamate to obtain serinol;
- and
- iii) optionally converting the serinol into a salt thereof.
Dependencies are inferred from the claim text.