Water → 1-Benzyl-3-phenyl-piperidin-3-ol

HRID 1861767

반응식

HRID 1861767 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1COCC1.O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:14])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 966503-Piperidinone, 1-(phenylmethyl)-HCID 178418255HCID 178418255, 화합물

생성물 1

HCID 3391281-Benzyl-3-phenyl-piperidin-3-ol수율 80%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

To a solution of 1-benzyl-3-piperidinone (0.193 g, 1.02 mmol) in toluene dry (10 mL) cooled at 0° C. was added a solution of phenyl magnesium bromide 3.0 M in THF (0.48 mL, 1.4 mmol). The resulting solution was maintained at 0° C. for 2 h, then was allowed to warm at 25° C. for 1 h. Water (50 mL) was added and the mixture was extracted with EtOAc (2×50 mL). The collected organic phase was dried and concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel using EtOAc/cyclohexane as eluant to afford the title compound as a white solid (0.235 g, 80%). 1H NMR (CDCl3): 1.65-1.85 (m, 3H), 1.9-2.15 (m, 1H), 2.067 (bd, J=8.1Hz, 1H), 2.34 (d, J=11.1 Hz, 1H), 2.77 (d, J=11.1 Hz, 1H), 2.95 (bd, J=8.1Hz, 1H), 3.60 (s, 2H), 4.005 (bs, 1H), 7.2-7.4 (m, 8H), 7.50 (s, 1H), 7.525 (s, 1H).

후처리

  1. temperatureThe resulting solution was maintained at 0° C. for 2 h
  2. temperatureto warm at 25° C. for 1 h
  3. extractionthe mixture was extracted with EtOAc (2×50 mL)
  4. customThe collected organic phase was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude compound was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-33b1159a9a9e4b3aa6101e9598d4bd07
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06534522B2

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