Propylene Oxide → 1-[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-propan-2-ol
Reaction equation
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]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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).
Workup
- additionwas added
- customwas allowed to slowly reach room temperature
- stirringwhile being stirred overnight
- customThe reaction was quenched with NH4Cl, pH
- extractionfollowed by an extraction with EtOAc (4×)
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bfae3bb45baf43808f2e7529f7f9209f
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07393865B2
Reaction notes
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