FIELD

The present technology is generally related to a process for preparing amino alcohols. In particular, the present technology relates to a process for preparing 1,2-amino alcohols from the hydroxylation or acyloxylation of primary alkyl amines.

SUMMARY

In an aspect of the present technology, a process for preparing an amino alcohol is provided, the process comprising: condensing a compound of Formula (II), a stereoisomer, a tautomer, or a salt thereof with a compound of Formula (IIIa) or Formula (IIIb), a stereoisomer, a tautomer, or a salt thereof to form a condensation product; hydroxylating or acyloxylating the condensation product in the presence of an oxidant to obtain a hydroxylation or acyloxylation product; and subjecting the hydroxylation or acyloxylation product to one or more subsequent reactions comprising a hydrolysis reaction, alcohol deprotection, an aminolysis reaction, or a combination of two or more thereof to obtain an amino alcohol of Formula (I); wherein:



In the above structures, L is a carbonyl, imine, acetal, or hemiacetal; X is an amine or a protected amine; R1, R2, R3, and R4are each independently a hydrogen, a substituted or unsubstituted C1-C10alkyl, a substituted or unsubstituted C3-C10cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted heteroaryl, or two or more of R1, R2, R3, and R4together with the atoms to which they are attached form a substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aromatic, or substituted or unsubstituted heteroaromatic ring; R5is a hydrogen, halogen, a hydroxyl, an alkoxy, an O-acyl, a substituted or unsubstituted C1-C10alkyl, a substituted or unsubstituted C3-C10cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heterocyclyl, or a substituted or unsubstituted heteroaryl; R6is a hydrogen, a substituted or unsubstituted C1-C10alkyl, a substituted or unsubstituted C3-C10cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heterocyclyl, or a substituted or unsubstituted heteroaryl; R7and R8in Formula (IIIa) are each independently a hydrogen, a substituted or unsubstituted C1-C10alkyl, a substituted or unsubstituted C3-C10cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted heteroaryl, or R7and R8together with the atoms to which they are attached form a substituted or unsubstituted aromatic or heteroaromatic ring; and R7a, R7b, R8a, and R8bin Formula (IIIb) are each independently a hydrogen, a substituted or unsubstituted C1-C10alkyl, a substituted or unsubstituted C3-C10cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted heteroaryl, or two or more of R7a, R7b, R8a, and R8btogether with the atoms to which they are attached form a substituted or unsubstituted cycloalkyl or heterocyclyl ring.

