Ammonium Hydroxide → Benzyl 2-(4-chlorophenyl)-4-oxopiperidine-1-carboxylate

HRID 15729

반응식

HRID 15729 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[B-](F)(F)(F)[O+](C)C.[O:17]=[C:18]1[CH:23]=[CH:22][N:21]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:20][CH2:19]1.[NH4+].[Cl-].[NH4+].[OH-]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:22]2[CH2:23][C:18](=[O:17])[CH2:19][CH2:20][N:21]2[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 11368235Benzyl 3,4-dihydro-4-oxo-pyridine-1(2H)-carboxylateHCID 178478191HCID 178478191, 화합물HCID 178494437HCID 178494437, 화합물

생성물 1

HCID 59342393Benzyl 2-(4-chlorophenyl)-4-oxopiperidine-1-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

CuBr.SMe2 complex (1.49 g, 7.26 mmol) was added to 25 mL of anhydrous THF and cooled to −78° C. 4-Chlorophenylmagnesium bromide (7.26 mL, 1.0 M in THF, 7.26 mmol) was added slowly via syringe. Stirring at −78° C. for 1 hour produced an orange then green-like suspension. Boron trifluoride dimethyl etherate (0.92 mL, 7.26 mmol) was added and stirred for 5 minutes. To the newly formed complex was then added over 1 hour a solution of the compound 66 (1.0 g, 4.32 mmol) in 15 mL of anhydrous THF. After stirring 2 hours at −78° C., 16 mL of aq. 20% NH4Cl/conc. NH4OH (1:1) was added, and the mixture was allowed to warm-up to room temperature. EtOAc was used to extract (3×100 mL) and the combined organic layers were washed with brine and dried (MgSO4). Solvent was removed by rotary evaporation and the residue was purified by flash chromatography to give the product 67 as a colorless oil.

후처리

  1. customproduced an orange then green-like suspension
  2. stirringstirred for 5 minutes
  3. stirringAfter stirring 2 hours at −78° C.
  4. temperatureto warm-up to room temperature
  5. extractionto extract (3×100 mL)
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. customSolvent was removed by rotary evaporation
  9. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-ab71bfae619241b3a6352d150f024773
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732609B2

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