Preparation of optically active 1,3-dioxolane-4-methanol compoun

Details Preparation of optically active 1,3-dioxolane-4-methanol compoun Preparation of optically active 1,3-dioxolane-4-methanol compoun

1984-02-15

1986-03-11

Love, Ethel G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

562587, C07D31700, C07C 5910, C07C 59285

Patent

active

045755582

ABSTRACT:
Described is a process for preparing 2,2'-disubstituted-1,3-dioxolane-4-methanol compounds having the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently hydrogen, alkyl, cycloalkyl or R.sub.1 and R.sub.2 together with the carbon atom form a 3 to 6 member cycloalkyl group, or aryl, the process comprising: reacting D- or L-serine with a nitrosating agent in an aqueous solution in the presence of formic acid, acetic acid, or propanoic acid to prepare 2,3-dihydroxypropanoic acid (D- or L-glyceric acid), the aqueous solution comprising from about 0.1 to 0.5 liter of water per mole of the serine starting material; reacting the glyceric acid so formed with 2,2-dimethoxypropane in the presence of a loweralkyl alcohol to prepare the D- or L-glyceric acid alkyl ester which is reacted with a selected aldehyde or ketone or the acetal or ketal derivative to prepare the corresponding 1,3-dioxolane derivative. Reacting the 1,3-dioxolane derivative with lithium aluminum hydride provides the desired 2,2'-disubstituted-1,3-dioxolane-4-methanol derivative.
If an alcohol is not used as described above, then the 2,3-dihydroxypropanoic acid is reacted with a selected aldehyde or ketone or the acetal or ketal derivative to prepare the 1,3-dioxolane derivative. The dioxolane derivative is then reacted with lithium aluminum hydride to provide the desired 2,2'-disubstituted-1,3-dioxolane-4-methanol derivative.
The compounds so prepared are intermediates in the preparation of optically active beta-agonists or antagonists.

REFERENCES:
patent: 3058981 (1962-10-01), Avakian et al.
Lok et al, Chemistry and Physics of Lipids 16 (1976) pp. 115-122.

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