US 7,402,709 B2Granted

Process for synthesizing heliotropine and its derivatives

AssigneeEndura S.p.A.

InventorsValerio Borzatta, Elisa Capparella, Carlotta Gobbi, Elisa Poluzzi

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Abstract

A new high-yield, easily industrialized process for synthesizing compounds of formula (IV), in which X1 and X2, the same or different, are linear or branched C1-C8 alkyls, n and m are 0, 1 or 2, with the proviso that n and m are not simultaneously 0; or (OX1)n and (OX2)m taken together form an O-T-O group where T is chosen from —CH2—, —CH2CH2, —CH2CH2CH2—, —C(CH3)2—. The process comprises treating a chloromethyl derivative (I) with an alkaline acetate to form the intermediate acetylderivative (II); the intermediate (II) is to hydrolysed to form the alcohol (III); the alcohol (III) is then oxidised in the presence of air and catalysts to obtain the desired derivative (IV). The process runs its course within a short period of time, with high yields and high selectivity; in addition, the process does not require purification and separation of the intermediates and can therefore be favourably conducted in a single batch.

Claims9

Dependent claims

Process for obtaining a compound of formula (IV)

in which X1 and X2, the same or different, are linear or branched C1-C8 alkyls, n and m are 0, 1 or 2, with the proviso that n and m cannot be simultaneously 0;
or (OX1)n and (OX2)m taken together form an O-T-O group where T is chosen from —CH2—, —CH2CH2—, —CH2CH2CH2—, —C(CH3)2—,
said process comprising the following passages:
(i) treating a chloromethyl derivative of formula (I) with an alkaline acetate to form the acetyl derivative of formula (II), where X1, X2, m and n have the aforesaid meanings;
(ii)hydrolyzing compound (II) to form the alcohol (III), where X1, X2, m and n have the aforesaid meanings;
(iii) catalytic oxidation of the alcohol (III) to form the compound (IV)
wherein the passage (iii) is conducted by treating in the liquid phase the product of passage (ii) with air or oxygen and an alkaline hydroxide used in a hydroxide/alcohol (III) equivalent ratio between 1 and 2, in the presence of a suitable oxidation catalyst.

4 more elements

Dependencies are inferred from the claim text.