2-Furancarbonyl chloride → HCID 131731968, compound

HRID 539421Notes

Reaction equation

HRID 539421 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.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[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]([C:13]1[O:12][CH:16]=[CH:15][CH:14]=1)=[O:18])([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]([C:13]1[O:12][CH:16]=[CH:15][CH:14]=1)=[O:18])([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 89497Cyclohexanamine, 5-methyl-2-(1-methylethyl)-3×

Product 1

HCID 131731968HCID 131731968, compound

Procedure

The aforementioned product is obtained as a colorless solid containing in total 94.7% of the desired neomenthylamine derivatives from racemic neomenthylamine, as in the GP, by reaction with furan-2-carbonyl chloride. Furthermore, two further isomeric menthylamine derivatives are present at 3.8% and 1.3%, corresponding to a purity over all stereoisomers of 99.8%.

Workup

  1. customThe aforementioned product is obtained as a colorless solid

Sources & evidence

ORD record
ord-433b1a0abe4f4abcaebbe742fce36f7a
Source dataset
uspto-grants-2014_10
Patent number
US08871288B2

Reaction notes

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