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

HRID 1367790Notes

Reaction equation

HRID 1367790 reaction equation
[CH3:1][C@:2]12[C:11]3=[CH:12][CH2:13][C@@:14]([CH:17]=[CH2:18])([CH3:16])[CH2:15][CH:10]3[CH2:9][CH2:8][CH:7]1[C@@:6]([C:20]([OH:22])=[O:21])([CH3:19])[CH2:5][CH2:4][CH2:3]2.C(Cl)(C(Cl)=O)=O.[CH:29]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl.CN(C=O)C>[CH:29]1([NH-:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.[CH3:1][C@:2]12[C:11]3=[CH:12][CH2:13][C@@:14]([CH:17]=[CH2:18])([CH3:16])[CH2:15][CH:10]3[CH2:9][CH2:8][CH:7]1[C@@:6]([C:20]([OH:22])=[O:21])([CH3:19])[CH2:5][CH2:4][CH2:3]2

Participants

7

Reactant 3

HCID 7965CyclohexylamineHCID 65578Oxalyl chlorideHCID 9861219(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

Product 2

HCID 9861219(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 19097440HCID 19097440, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. customobtained by the
  2. customWhen the reaction stops bubbling
  3. customthe CH2Cl2 solvent and (COCl)2 can be evaporated under vacuum
  4. dissolutionthe reaction residue can be redissolved in dry benzene

Sources & evidence

ORD record
ord-995e26023f3248e3a8a80ae8f6747547
Source dataset
uspto-grants-2011_02
Patent number
US07893299B2

Reaction notes

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