Triethylamine → [(1S,4aS,7R)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-1-phenanthrenyl](1-pyrrolidinyl)methanone

HRID 1367792Notes

Reaction equation

HRID 1367792 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](O)=[O:21])([CH3:19])[CH2:5][CH2:4][CH2:3]2.C(Cl)(=O)C(Cl)=O.[CH2:29]([N:31](CC)[CH2:32][CH3:33])[CH3:30].N1CCCC1>C(Cl)Cl.CN(C=O)C>[CH3:19][C@@:6]1([C:20]([N:31]2[CH2:32][CH2:33][CH2:30][CH2:29]2)=[O:21])[CH:7]2[C@@:2]([CH3:1])([C:11]3[CH:10]([CH2:9][CH2:8]2)[CH2:15][C@:14]([CH3:16])([CH:17]=[CH2:18])[CH2:13][CH:12]=3)[CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 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 1

HCID 57485008[(1S,4aS,7R)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-1-phenanthrenyl](1-pyrrolidinyl)methanoneYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of acanthoic acid 1 (30 mg, 0.10 mmol) in CH2Cl2 (3.0 ml) was treated with oxalyl chloride (0.013 ml, 0.15 mmol) in the presence of a catalytic amount of DMF at room temperature. The reaction mixture was stirred for 3 h at room temperature, distilled under reduced pressure, and then 3 ml of CH2Cl2 was added. Triethylamine (0.03 ml, 0.20 mmol) and pyrrolidine (0.02 ml, 0.20 mmol) were added to the reaction mixture. The reaction mixture was stirred for 30 min., quenched with water and extracted with 5 ml of CH2Cl2. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10) to afford 25 mg of the analog 2 (71%).

Workup

  1. distillationdistilled under reduced pressure
  2. addition3 ml of CH2Cl2 was added
  3. stirringThe reaction mixture was stirred for 30 min.
  4. customquenched with water
  5. extractionextracted with 5 ml of CH2Cl2
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10)

Sources & evidence

ORD record
ord-7d9661a71bca4894afd6b4aae8e54567
Source dataset
uspto-grants-2011_02
Patent number
US07893299B2

Reaction notes

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