Tetrahydrofuran → HCID 21939877、化合物

HRID 1242950ノート

反応式

HRID 1242950 の反応式
[Cl-].C[CH:3]=[N+:4]=[CH:5]C.[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([NH:22][C:23]3[CH:32]=[CH:31][C:30]4[C:29](=[O:33])[CH2:28][CH2:27][CH2:26][C:25]=4[CH:24]=3)=[O:21])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[BH4-].[Na+].O1CCC[CH2:37]1>C(#N)C>[CH3:3][N:4]([CH2:5][CH:28]1[CH2:27][CH2:26][C:25]2[CH:24]=[C:23]([NH:22][C:20]([N:17]3[CH2:18][CH2:19][CH:14]([C:11]4[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=4)[CH2:15][CH2:16]3)=[O:21])[CH:32]=[CH:31][C:30]=2[CH:29]1[OH:33])[CH3:37]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 21873455N,N-dimethylmethylene ammonium chlorideHCID 21939957HCID 21939957、化合物

生成物 1

HCID 21939877HCID 21939877、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

N,N-Dimethylmethylene ammonium chloride(638 mg, 6.82 mmol) was added to a mixed solution of 4-(4-fluorophenyl)-N-(5-oxo-5,6,7,8-tetrahydro-2-naphthalenyl)-1-piperidinecarboxamide (1.00 g, 2.73 mmol) obtained in Reference Example 97 in tetrahydrofuran (10 ml) and acetonitrile (10 ml), which was stirred at room temperature for 1 day. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, which was washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was dissolved in methanol (15 ml). Sodium borohydride (103 mg, 2.73 mmol) was added to the solution under ice-cooling, which was stirred for 1 hour. Then, the solvent was distilled out under reduced pressure. 1N Hydrochloric acid was added to the residue, which was washed with ethyl acetate. 4N Sodium hydroxide was added to the water layer to make it alkaline. The reaction mixture was extracted with ethyl acetate, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting residue was purified by aluminum B column chromatography (development solvent; ethyl acetate), powdered with hexane, to give the titled compound (231 mg).

後処理

  1. distillationThe solvent was distilled out under reduced pressure
  2. additionEthyl acetate was added to the residue, which
  3. washwas washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. dissolutionThe resulting oily substance was dissolved in methanol (15 ml)
  7. temperaturecooling
  8. distillationThen, the solvent was distilled out under reduced pressure
  9. addition1N Hydrochloric acid was added to the residue, which
  10. washwas washed with ethyl acetate
  11. addition4N Sodium hydroxide was added to the water layer
  12. extractionThe reaction mixture was extracted with ethyl acetate, which
  13. washwas washed with saturated aqueous sodium chloride solution
  14. dry with materialdried over anhydrous sodium sulfate
  15. distillationthe solvent was distilled out under reduced pressure
  16. customThe resulting residue was purified by aluminum B column chromatography (development solvent; ethyl acetate)

出典と根拠

ORDレコード
ord-5012c7cbd72a4ab5a62fbddd6dd6bec1
出典データセット
uspto-grants-2006_10
特許番号
US07115750B1

反応ノート

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