Water → 1'-benzyl-5-methyl-3H-spiro[1-benzofuran-2,4'-piperidine]

HRID 270038

반응식

HRID 270038 반응식
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]([CH2:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=2F)([OH:16])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN(C=O)C.O>C1(C)C=CC=CC=1>[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]2([CH2:17][C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=3[O:16]2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 598336351-Benzyl-4-(2-fluoro-5-methylbenzyl)piperidin-4-ol

생성물 1

HCID 598336331'-benzyl-5-methyl-3H-spiro[1-benzofuran-2,4'-piperidine]수율 41%

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
110 °C

실험 절차

To a suspension of NaH (55% in mineral oil, 200 mg, 5 mmol) in toluene (10 mL) was slowly added a solution of crude 1-benzyl-4-(2-fluoro-5-methylbenzyl)piperidin-4-ol in toluene (15 mL). After addition was completed, the reaction mixture was heated to 110° C. and stirred for 5 min. DMF (9 mL) was added and stirring was continued at reflux temperature for 10 h. The reaction mixture was cooled to room temperature, poured into water (50 ml), and extracted with ethyl acetate (2×25 ml). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (ethyl acetate/n-heptane) to give the subtitle compound (240 mg, 41%).

후처리

  1. additionAfter addition
  2. stirringstirring
  3. temperatureat reflux temperature for 10 h
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionextracted with ethyl acetate (2×25 ml)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel flash chromatography (ethyl acetate/n-heptane)

출처 및 근거

ORD 기록
ord-260f62b0aab84857b4fdc4e95d4293a3
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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