Veratroyl chloride → HCID 86629951, compound

HRID 539422Notes

Reaction equation

[CH3:1][CH:2]1[CH2:7][CH:6]([NH2:8])[CH:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:17](Cl)=[O:18]>>[CH:9]([C@@H:5]1[CH2:4][CH2:3][C@@H:2]([CH3:1])[CH2:7][C@@H:6]1[NH:8][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:14]([O:13][CH3:12])[CH:15]=1)([CH3:11])[CH3:10].[CH:9]([C@H:5]1[CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:7][C@H:6]1[NH:8][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:14]([O:13][CH3:12])[CH:15]=1)([CH3:11])[CH3:10]

Participants

Reactant 2

HCID 77070Veratroyl chloride

HCID 89497Cyclohexanamine, 5-methyl-2-(1-methylethyl)-3×

Product 1

HCID 86629951HCID 86629951, compound

Procedure

The aforementioned product is obtained as a colorless solid containing in total 97.8% of the desired neomenthylamine derivatives from racemic neomenthylamine, as in the GP, by reaction with 3,4-dimethoxybenzoylchloride. Furthermore, two further isomeric menthylamine derivatives are present at 1.3% and 0.9%, corresponding to a purity over all stereoisomers of 100.0%.

Workup

customThe aforementioned product is obtained as a colorless solid

Sources & evidence

ORD record: ord-35c8567deb714321bb7fc5e9cbb0f60c
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871288B2

Reaction notes

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