Hydrochloric Acid → 1'-Benzyl-6-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]

HRID 270049ノート

反応式

HRID 270049 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=3[C:15](=O)[O:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.Cl.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=3[CH2:15][O:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14798Sodium HydroxideHCID 122130471'-Benzyl-6-chloro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

生成物 1

HCID 598336401'-Benzyl-6-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]収率 85.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 1′-benzyl-6-chloro-3H-spiro[2-benzofuran-1,4′-piperidine]-3-one (1.1 g, 3.35 mmol) in THF (15 mL) was added 1 M solution of borane (Marxer, A; Rodriguez, H. R; McKenna, J. M; Tsai, H. M., J. Org. Chem., 1975, 40, 1427-1430) complex in THF (7 mL, 7.0 mmol) slowly at 0° C. After addition was complete, the reaction mixture was kept at room temperature for 30 minutes (min), then kept at reflux overnight, cooled to 0° C. and 6M aqueous hydrochloric acid (HCl) (3.5 mL) was added slowly. The reaction mixture was kept at reflux for 5 h, cooled to 0° C., pH of the reaction mixture was adjusted to 10 by addition of aqueous NaOH 6M and the whole was extracted with ethyl acetate. The organic layer was washed with H2O, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum ether) to give the sub-titled compound (900 mg).

後処理

  1. customslowly at 0° C
  2. additionAfter addition
  3. temperatureat reflux overnight
  4. temperatureat reflux for 5 h
  5. temperaturecooled to 0° C.
  6. extractionthe whole was extracted with ethyl acetate
  7. washThe organic layer was washed with H2O
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-48d79ac957244662a374a36991338cf2
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

反応ノート

読み込み中…