# US 5,352,811 A · Method of preparing alkanoyloxytetrodecanoic acid by assymmetric allylboratron

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- Number: US 5,352,811 A
- Document ID: US5352811A
- Status: Granted
- Kind: A
- Application number: 07/916,664
- Filed: 1992-07-22
- Granted: 1994-10-04
- Earliest claimed: 1990-06-08
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: Prabhakar K. Jadhav
- Web page: https://patentgrep.com/patent/US5352811A

## CPC

- A61K 31/7004: Monosaccharides having only carbon, hydrogen and oxygen atoms
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

Preparaing alkanoyloxytetradecanoic acids by asymmetric allylboration, acylation, and oxidation of homoallylic alcohols in the operational presence of a phase transfer catalyst.

## Claims

### Claim 1

A process for synthesizing a compound of structure: ##STR19## comprising the following steps: (a) asymmetric allylboration of 1-dodecanal resulting in a homoallylic alcohol;
(b) acylation of the homoallylic alcohol; and
(c) oxidation of the olefinic moiety to carboxylic acid in the optional presence of a phase transfer catalyst.

### Claim 2 (depends on 1)

The process of claim 1 wherein the oxidation of the olefinic moiety to carboxylic acid is done with permanganate.

### Claim 3 (depends on 1)

The process of claim 1 wherein the allylboration of 1-dodecanal is done with allyldiisopinocamphelborane derived from dextro-.alpha.-pinene.

### Claim 4 (depends on 1)

The process of claim 1 wherein the allylboration of 1-dodecanal is done with an allylboration reagent synthesized from levo-.alpha.-pinene.