Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1094474Generated: October 31, 2026

Cyclohexylamine → (1R,4aR,7S)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid

https://huagongshe.com/reaction/1094474

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCyclohexylamineHCID 7965—
ReactantOxalyl chlorideHCID 65578—
Reactant(1R,4aR,7S)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acidHCID 9861219—
CatalystDimethylformamideHCID 6228—
SolventDichloromethaneHCID 6344—
Product(1R,4aR,7S)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acidHCID 9861219—
ProductHCID 19097440HCID 19097440—

Reaction Steps

Acanthoic acid, including compound obtained by the above described methodology, can be dissolved in dry CH2Cl2 and treated with 10 equivalents of (COCl)2 followed by two drops of DMF. When the reaction stops bubbling, the CH2Cl2 solvent and (COCl)2 can be evaporated under vacuum and the reaction residue can be redissolved in dry benzene and then treated with 5 equivalents of cyclohexylamine to yield N-cyclohexylamide derivative of acanthoic acid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08133915B2
Source datasetuspto-grants-2012_03
ORD IDord-8c0339b93de64ef490700497f84031f5
Source noteuspto-grants-2012_03