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 1367792ノート

反応式

HRID 1367792 の反応式
[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

参加物

7

反応物 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

生成物 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)methanone収率 71%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-7d9661a71bca4894afd6b4aae8e54567
出典データセット
uspto-grants-2011_02
特許番号
US07893299B2

反応ノート

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