Phenol → (R)-2-methyl-1-(3-phenoxy-propyl)-pyrrolidine

HRID 2042656노트

반응식

HRID 2042656 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][CH2:10][CH2:11]Cl.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:20][C@@H:21]1[CH2:25][CH2:24][CH2:23][NH:22]1.[I-].[Na+]>C(#N)C>[CH3:9][C@@H:10]1[CH2:11][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][CH2:25][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 5

HCID 996PhenolHCID 5238Sodium IodideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 11147704(2R)-(-)-2-Methylpyrrolidine hydrochloride

생성물 1

HCID 67009682(R)-2-methyl-1-(3-phenoxy-propyl)-pyrrolidine수율 77.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a round-bottom flask was added phenol (5.0 g, 53.1 mmol), 1-bromo-3-chloropropane (5.52 mL, 55.8 mmol), potassium carbonate (22.0 g, 159 mmol), and acetonitrile (100 mL). The reaction mixture was heated to reflux for 15 h. To this reaction was then added (R)-2-methyl-pyrrolidine hydrochloride (12.9 g, 106 mmol) and sodium iodide (7.96 g, 53.1 mmol) at room temperature. The reaction was continued to reflux for 24 h. After cooled to room temperature, the reaction was filtered through a pad of Celite eluted with CH2Cl2 (100 mL). The filtrate was concentrated. Purification by column chromatography (5% MeOH in CH2Cl2) to give 9.02 g (77%) of (R)-2-methyl-1-(3-phenoxy-propyl)-pyrrolidine.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 15 h
  3. customat room temperature
  4. temperatureto reflux for 24 h
  5. filtrationthe reaction was filtered through a pad of Celite
  6. washeluted with CH2Cl2 (100 mL)
  7. concentrationThe filtrate was concentrated
  8. customPurification by column chromatography (5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-befb97223f9945d6b880a5d998e821de
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586588B2

반응 노트

불러오는 중…