Tetrahydrofuran → HCID 21939877, 화합물

HRID 1242950노트

반응식

HRID 1242950 반응식
[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]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 21873455N,N-dimethylmethylene ammonium chlorideHCID 21939957HCID 21939957, 화합물

생성물 1

HCID 21939877HCID 21939877, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5012c7cbd72a4ab5a62fbddd6dd6bec1
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115750B1

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