N-Methylephedrine → Menthol

HRID 374330

반응식

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

참가 물질

반응물 4

HCID 4374N-Methylephedrine

HCID 264821,2-Diphenylethylamine

HCID 2607082,2-Dimethylcyclopropane-1-carboxylic acid

HCID 3034034Quinine

생성물 1

HCID 1254Menthol

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록: ord-9ce85cc781f547289f414858807b168e
출처 데이터셋: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05166417

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