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Preparation of ((1S, 2R)-1-((R)-2, 2-dimethyl-1, 3-dioxolan-4-yl)-2-((4-methoxybenzyl) oxy) but-3-en-1-ol (Compound III a) in a mixture with isomer (1S, 2R)-1-((R)-2, 2-dimethyl-1, 3-dioxolan-4-yl)-1-((4-methoxybenzyl) oxy) but-3-en-2-ol (Compound III b)

IP.com Disclosure Number: IPCOM000238879D
Publication Date: 2014-Sep-23
Document File: 3 page(s) / 236K

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The IP.com Prior Art Database

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Preparation of ((1S, 2R)-1-((R)-2, 2-dimethyl-1, 3-dioxolan-4-yl)-2-((4- methoxybenzyl) oxy) but-3-en-1-ol (Compound III a)
in a mixture with isomer (1S, 2R)-1-((R)-2, 2-dimethyl-1, 3-dioxolan-4-yl)-1-((4- methoxybenzyl) oxy) but-3-en-2-ol (Compound III b)

    ((1S, 2R)-1-((R)-2, 2-dimethyl-1, 3-dioxolan-4-yl)-2-((4-methoxybenzyl) oxy) but-3-en-1-ol, referred as to 'Compound III a', has the following formula:

Compound III a

Isomer (1S, 2R)-1-((R)-2, 2-dimethyl-1, 3-dioxolan-4-yl)-1-((4-methoxybenzyl) oxy) but-3-en-2-ol, referred as to 'Compound III b' has the following formula:

    Described hereinafter, is the preparation of ((1S, 2R)-1-((R)-2, 2-dimethyl-1,3- dioxolan-4-yl)-2-((4-methoxybenzyl)oxy)but-3-en-1-ol Compound III a in a mixture with isomer (1S, 2R)-1-((R)-2, 2-dimethyl-1,3-dioxolan-4-yl)-1-((4- methoxybenzyl)oxy)but-3-en-2-ol (Compound III b), starting from (1S, 2R)-1-((R)-2, 2-dimethyl-1, 3-dioxolan-4-yl)but-3-ene-1, 2-diol (Compound I).

The process can be described by the following scheme:

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    For the purpose of clarity and as an aid in the understanding of the process, as disclosed herein, the following terms and abbreviations are defined below:

    Compound I (1S, 2R)-1-((R)-2, 2-dimethyl-1, 3-dioxolan-4-yl) but-3-ene-1, 2-diol

    Compound II (4R, 4'S, 5'R)-2'-(4-methoxyphenyl)-2, 2-dimethyl-5'-vinyl-4, 4'-bi (1, 3-dioxolane)

    Compound IIIa ((1S, 2R)-1-((R)-2, 2-dimethyl-1, 3-dioxolan-4-yl)-2- ((4-methoxybenzyl) oxy) but-3-en-1-ol

    Compound IIIb (1S, 2R)-1-((R)-2, 2-dimethyl-1, 3-dioxolan-4-yl)-1-((4- methoxybenzyl) oxy) but-3-en-2-ol

PMB - para-methoxybenzyl

PTSA- para-toluenesulfonic acid DMF-N, N-dimethylformamide MTBE-tert-butylmethyl ether DIBAl-H-diisobutylaluminium hydride DCM-dichloromethane

EtOAc-ethyl acetate

    The preparation of the starting material, (1S, 2R)-1-((R)-2, 2-dimethyl-1, 3- dioxolan-4-yl) but-3-ene-1, 2-diol (Compound I), can be done by methods known in the art. For example, (1S, 2R)-1-((R)-2, 2-dimethyl-1, 3-dioxolan-4-yl) but-3-ene-1, 2-diol can be prepared from D-Mannitol as described in previous publications IPCOM000225941D and IPCOM0002322556D). This compound can then be purif...