Hydrochloric Acid → 1'-Benzyl-5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]

HRID 270092ノート

反応式

HRID 270092 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][C:20]([Cl:22])=[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.Cl.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=3[CH2:15][O:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 598336431'-benzyl-5-chloro-3H-spiro[isobenzofuran-1,4'-piperidin]-3-one

生成物 1

HCID 598336321'-Benzyl-5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]収率 95.1%

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-5-chloro-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (1.1 g, 3.35 mmol) in THF (12 mL) was added 1 M solution of borane complex in THF (7 mL, 7.0 mmol) slowly at 0° C. After addition was complete reaction mixture was kept at room temperature for 30 min, then kept at reflux overnight, cooled to 0° C. and 6M aqueous 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 water, dried over sodium sulphate (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 subtitled compound (1.0 g).

後処理

  1. additionAfter addition
  2. temperatureat reflux overnight
  3. temperatureat reflux for 5 h
  4. temperaturecooled to 0° C.
  5. extractionthe whole was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over sodium sulphate (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. 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-4fa3fb46812240c59a78ebdd85624430
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

反応ノート

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