N-Methylephedrine → Menthol

HRID 374330

Reaktionsgleichung

Reaktionsgleichung von HRID 374330
COC1C=C[C:6]2N=CC=[C:9]([C@@H](O)[C@H]3N4C[C@H](C=C)[C@@H](CC4)C3)[C:7]=2[CH:8]=1.C1(C(N)CC2C=CC=CC=2)C=CC=CC=1.CC(N(C)C)C(O)C1C=CC=CC=1.[CH3:53][C:54]1([CH3:60])[CH2:56][CH:55]1[C:57](O)=[O:58]>>[CH:7]1([CH3:9])[CH2:8][CH2:56][CH:55]([CH:54]([CH3:60])[CH3:53])[CH:57]([OH:58])[CH2:6]1

Komponenten

5

Edukt 4

HCID 4374N-MethylephedrineHCID 264821,2-DiphenylethylamineHCID 2607082,2-Dimethylcyclopropane-1-carboxylic acidHCID 3034034Quinine

Produkt 1

HCID 1254Menthol

Versuchsvorschrift

With 1-phenylethylamine neither a satisfactory yield nor an adequate optical purity could be achieved. Quinine yielded enantiomer in good optical purity but poor yield, no yield was indicated for N-methylephedfine With 1,2-diphenylethylamine the yield is satisfactory and the optical purity very good but the reagent, as is also N-methylephedrine is very expensive. Further, it is known that 2,2-dimethylcyclopropanecarboxylic acid can be separated into the enantiomers by the diastereomeric menthyl esters, which can be obtained from the acid chloride with (+) or (-) menthol (U.S. Pat. No. 4,487,956). This process does provide usable yields and optical purities, but is relatively complicated in working up and requires the relatively expensive menthol.

Aufarbeitung

  1. customcan be separated into the enantiomers by the diastereomeric menthyl esters, which

Quellen und Nachweise

ORD-Eintrag
ord-9ce85cc781f547289f414858807b168e
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166417

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