1-Amino-2-propanol → HCID 87090848, compound
Reaction equation
[CH3:1][CH:2]([OH:5])[CH2:3][NH2:4].N1C=CN=C1.[Si:11](OS(C(F)(F)F)(=O)=O)([CH2:16][CH3:17])([CH2:14][CH3:15])[CH2:12][CH3:13].O>C1COCC1>[CH2:12]([Si:11]([CH2:16][CH3:17])([CH2:14][CH3:15])[O:5][CH:2]([CH3:1])[CH2:3][NH2:4])[CH3:13]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
In a 50 mL round bottomed flask, 1-methyl-2-aminoethanol (500.0 mg, 6.66 mmol) and imidazole (498.8 mg, 7.326 mmol, 1.1 equiv.) were dissolved in THF (3 mL). The mixture was cooled down to −78° C. and then TESOTf (1.76 g, 6.66 mmol, 1.0 equiv.) was added at the same temperature. The mixture was allowed to warm to room temperature. After stirring for 1 h, water (30 mL) was added to the mixture and the whole was extracted with EtOAc (30 mL×3). Combined organic layers were washed with brine (30 mL) and dried over Na2SO4. The solvent was removed under a reduced pressure to give the O-silylated aminoalcohol as a colorless oil (2-(triethylsilyloxy)propan-1-amine, 2.34 g). Obtained product was immediately used for the subsequent step.
Workup
- temperatureto warm to room temperature
- extractionthe whole was extracted with EtOAc (30 mL×3)
- washCombined organic layers were washed with brine (30 mL)
- dry with materialdried over Na2SO4
- customThe solvent was removed under a reduced pressure
Sources & evidence
- ORD record
- ord-45b6cc20c8aa40f0adf76b066134784a
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703759B2
Reaction notes
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