Water → HCID 21108202, compound
Reaction equation
[BH4-].[Na+].[C:3]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:21])[CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])[CH3:4].O>CO>[C:3]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]([OH:21])[CH2:16][CH2:17][N:18]([CH3:19])[CH3:20])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])[CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2.5 °C
Procedure
Sodium borohydride (0.75 g) was added to a solution of 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-3-(dimethylamino)-1-propanone (4.3 g) obtained in Reference Example 12 in methanol (40 ml) under cooling with ice-bath, and the mixture was stirred at 0 to 5° C. for 30 minutes. After iced water was added to the reaction solution, the solvent was distilled away under reduced pressure, and the residues were extracted with ethyl acetate. The extract was washed with a saturated saline solution and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The resultant residues were purified by alumina column chromatography (developing solvent; ethyl acetate), whereby 3-[1-acetyl-2,3-dihydro-1H-indol-5-yl]-3-hydroxy-N,N-dimethyl-1-propanamine (3.3 g) was obtained as colorless powder.
Workup
- temperatureunder cooling with ice-bath
- distillationthe solvent was distilled away under reduced pressure
- extractionthe residues were extracted with ethyl acetate
- washThe extract was washed with a saturated saline solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled away under reduced pressure
- customThe resultant residues were purified by alumina column chromatography (developing solvent; ethyl acetate)
Sources & evidence
- ORD record
- ord-a2eaba021c634cf892dd576950d6feaa
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07229986B2
Reaction notes
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