Intermediates in the epimerization of ritodrine by acid

Sill, A. D.; Housmyer, Carl L.; Gibboney, K.

doi:10.1016/s0040-4020(01)90058-4

Cited by 4 publications

(1 citation statement)

References 6 publications

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“…The synthesis of a spiropiperidine dienone similar to trans - 17a has been reported, and it is noteworthy that although the cyclization precursor is very similar to amino alcohol 15a , the formation of a 3-benzazepine product was not observed. Moreover, the product spiropiperidine dienone was reported to be unstable in strong acid or base and rapidly reverted to starting material upon exposure to 0.1 N aqueous HCl.…”

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Two General Routes to 1,4-Disubstituted-2,3,4,5-tetrahydro- 1H-3-benzazepines

et al. 2000

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[structure] Two general routes to 1,4-disubstituted-2,3,4, 5-tetrahydro-1H-3-benzazepines are described. Both routes utilize an appropriately functionalized phenethylamino alcohol as the penultimate intermediate: the first route makes use of the reductive amination of a benzyl alkyl ketone with alpha-(aminomethyl)benzyl alcohol, while the second route utilizes the addition of a Grignard reagent to the oxazolidine derived from a substitued phenylacetaldehyde and alpha-(methylaminomethyl)benzyl alcohol. In all cases studied, the cis-1,4-disubstituted-2,3,4, 5-tetrahydro-1H-3-benzazepine was obtained as the major product.

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Two General Routes to 1,4-Disubstituted-2,3,4,5-tetrahydro- 1H-3-benzazepines

et al. 2000

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ChemInform Abstract: Intermediates in the Epimerization of Ritodrine by Acid.

Sill¹,

Housmyer²,

Gibboney³

1987

ChemInform

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330ChemInform Abstract In contrast to l-epinephrine which undergoes racemization in aqueous HCl, ritodrine hydrochloride (I) is converted to its corresponding enantiomer (IV). The intermediate (II), obtained after evaporating an aqueous HCl solution of (I), is rapidly converted to the trans compound (III) on treatment with water. (III) is more stable in water and in 0.1 N AcOH or H3BO3 but is rapidly converted to (IV) in the presence of stronger acid or base.

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