3-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]cyclohexanone → 1-[(3-Phenyl-3-cyclohexenyl)methyl]-4-phenyl-1,2,3,6-tetrahydropyridine

HRID 1034191ノート

反応式

HRID 1034191 の反応式
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][C:16](=O)[CH2:15]3)[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]1([Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH:14]3[CH2:19][CH2:18][CH:17]=[C:16]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:15]3)[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 117778783-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]cyclohexanoneHCID 178418255HCID 178418255、化合物

生成物 1

HCID 104492741-[(3-Phenyl-3-cyclohexenyl)methyl]-4-phenyl-1,2,3,6-tetrahydropyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]cyclohexanone (Example A) (5.9 g) in 400 mL of tetrahydrofuran is added a solution of phenylmagnesium bromide (9.13 mL, 3.0M in diethyl ether), dropwise under nitrogen, at 0° C. The mixture is stirred at room temperature for 1 hour, then cooled in an ice bath and quenched with 250 mL of 10% aqueous hydrochloric acid solution. The solvent is evaporated in vacuo and the residue partitioned into chloroform/5% aqueous ammonium hydroxide solution. The organic extract is dried over magnesium sulfate and filtered. The filtrate is treated with trifluoroacetic acid (4.2 mL) and stirred overnight at room temperature. The solvent is evaporated in vacuo, and the residue is partitioned into ethyl acetate/5% aqueous ammonium hydroxide solution. The organic extract is dried over magnesium sulfate, filtered, and concentrated. The crude product is purified by medium pressure chromatography to give 3.9 g of (±) -1,2,3,6-tetrahydro-4-phenyl-1-[(3-phenyl-3-cyclohexen-1-yl)methyl]pyridine; mp 90°-95° C. as an off-white solid (Example 1) and 2.7 g of (±)-1,2,3,6-tetrahydro-4-phenyl-1-[(3-phenyl-2-cyclohexen-1-yl)methyl]pyridine; mp 124°-126° C. as a tan solid (Example 1a).

後処理

  1. customat 0° C
  2. temperaturecooled in an ice bath
  3. customquenched with 250 mL of 10% aqueous hydrochloric acid solution
  4. customThe solvent is evaporated in vacuo
  5. customthe residue partitioned into chloroform/5% aqueous ammonium hydroxide solution
  6. extractionThe organic extract
  7. dry with materialis dried over magnesium sulfate
  8. filtrationfiltered
  9. additionThe filtrate is treated with trifluoroacetic acid (4.2 mL)
  10. stirringstirred overnight at room temperature
  11. customThe solvent is evaporated in vacuo
  12. customthe residue is partitioned into ethyl acetate/5% aqueous ammonium hydroxide solution
  13. extractionThe organic extract
  14. dry with materialis dried over magnesium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated
  17. customThe crude product is purified by medium pressure chromatography

出典と根拠

ORDレコード
ord-93113b1a39eb4f2ab386e8079ab791cb
出典データセット
uspto-grants-1994_05
特許番号
US05314896

反応ノート

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