Propylene Oxide → 1-[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-propan-2-ol

HRID 746629노트

반응식

HRID 746629 반응식
Br[C:2]1[C:3]2[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=2[S:5][C:6]=1[CH2:7][CH2:8][N:9]([CH3:11])[CH3:10].CN(CCN(C)C)C.[Li]CCCC.[CH3:29][CH:30]1[CH2:32][O:31]1>C1(C)C=CC=CC=1>[CH3:10][N:9]([CH3:11])[CH2:8][CH2:7][C:6]1[S:5][C:4]2[CH:12]=[CH:13][CH:14]=[CH:15][C:3]=2[C:2]=1[CH2:29][CH:30]([OH:31])[CH3:32]

참가 물질

6

반응물 4

HCID 6378Propylene OxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 58591562[2-(3-Bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amineHCID 178418339Butyllithium

생성물 1

HCID 585915821-[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-propan-2-ol수율 17.5%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
-78 °C

실험 절차

A solution of [2-(3-bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amine (285 mg, 1 mmol) and TMEDA (181 uL, 1.2 mmol) in toluene (12 mL) was cooled to −78° C. n-BuLi (750 uL, 1.2 mmol, 1.6M in hexanes) was added and the reaction was stirred at −78° C. for 45 min. 2-Methyl-oxirane (280 uL, 4 mmol) was added at −78° C. and the reaction was allowed to slowly reach room temperature, while being stirred overnight. The reaction was quenched with NH4Cl, pH was adjusted with sat. NaHCO3 until pH ˜9, followed by an extraction with EtOAc (4×). The combined organic layers were washed with brine, dried (MgSO4) and concentrated. Silica gel column chromatography (eluent: dichloromethane with gradient up to dichloromethane/MeOH=97/3) afforded 46 mg of 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-propan-2-ol (Compound 23-1).

후처리

  1. additionwas added
  2. customwas allowed to slowly reach room temperature
  3. stirringwhile being stirred overnight
  4. customThe reaction was quenched with NH4Cl, pH
  5. extractionfollowed by an extraction with EtOAc (4×)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bfae3bb45baf43808f2e7529f7f9209f
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393865B2

반응 노트

불러오는 중…