Boron trifluoride etherate → 1,3,3-trimethyl-3H-spiro[isobenzofuran-1,4-piperidine]

HRID 1179279노트

반응식

HRID 1179279 반응식
O[C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1([OH:18])[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1)([CH3:4])[CH3:3].B(F)(F)F.CCOCC>C1C=CC=CC=1>[CH3:17][N:14]1[CH2:13][CH2:12][C:11]2([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:2]([CH3:3])([CH3:4])[O:18]2)[CH2:16][CH2:15]1

참가 물질

4

반응물 2

HCID 8000Boron trifluoride etherateHCID 122896704-[2-(1-Hydroxy-1-methylethyl)phenyl]-1-methylpiperidin-4-ol

생성물 1

HCID 122896791,3,3-trimethyl-3H-spiro[isobenzofuran-1,4-piperidine]수율 56%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

To a stirred solution of 4-[2-(1-hydroxy-1-methylethyl)phenyl]-1-methylpiperidin-4-ol (step 2, 4.62 g, 18.5 mmol) in benzene (200 mL) was added dropwise boron trifluoride diethyl etherate (11.0 mL, 86.8 mmol) at room temperature and the mixture was stirred for 40 h at the same temperature. The reaction mixture was quenched by the addition of water (200 mL) and 2 N sodium hydroxide aqueous solution (200 mL), and the benzene layer was separated. The aqueous layer was extracted with diethyl ether, and then combined organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on an amine coated silica gel (100 g) eluting with dichloromethane to afford 2.39 g (56%) of the title compound as a colorless solid:

후처리

  1. customThe reaction mixture was quenched by the addition of water (200 mL) and 2 N sodium hydroxide aqueous solution (200 mL)
  2. customthe benzene layer was separated
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. washcombined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography on an amine coated silica gel (100 g)
  8. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-c6d0ebb70e264e4bb73029f93fad991b
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279486B2

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