Hydrochloric Acid → 1'-Benzyl-6-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]

HRID 270049노트

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HRID 270049 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[C:19]([Cl:22])[CH:20]=[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.B.Cl.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=3[CH2:15][O:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14798Sodium HydroxideHCID 122130471'-Benzyl-6-chloro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

생성물 1

HCID 598336401'-Benzyl-6-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]수율 85.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution of 1′-benzyl-6-chloro-3H-spiro[2-benzofuran-1,4′-piperidine]-3-one (1.1 g, 3.35 mmol) in THF (15 mL) was added 1 M solution of borane (Marxer, A; Rodriguez, H. R; McKenna, J. M; Tsai, H. M., J. Org. Chem., 1975, 40, 1427-1430) complex in THF (7 mL, 7.0 mmol) slowly at 0° C. After addition was complete, the reaction mixture was kept at room temperature for 30 minutes (min), then kept at reflux overnight, cooled to 0° C. and 6M aqueous hydrochloric acid (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 H2O, dried over 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 sub-titled compound (900 mg).

후처리

  1. customslowly at 0° C
  2. additionAfter addition
  3. temperatureat reflux overnight
  4. temperatureat reflux for 5 h
  5. temperaturecooled to 0° C.
  6. extractionthe whole was extracted with ethyl acetate
  7. washThe organic layer was washed with H2O
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-48d79ac957244662a374a36991338cf2
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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