Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Amino-1-propanol | HCID 9086 | — |
| Reactant | tert-Butyl bromoacetate | HCID 79177 | — |
| Reactant | Triisopropylsilyl trifluoromethanesulfonate | HCID 2724529 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86673313 | HCID 86673313 | 25.7% |
Reaction Steps
To a solution of 3-amino-1-propanol (2.0 mL, 26 mmol) in dichloromethane (20 mL) was added triisopropylsilyl trifluoromethanesulfonate (7.2 mL, 27 mmol), and the mixture was stirred at room temperature for 1 hour. Triethylamine (3.7 mL, 26 mmol) and bromoacetic acid tert-butyl ester (3.1 mL, 21 mmol) were added to the reaction mixture, and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (dichloromethane/methanol=97/3) to give the title compound (1.85 g, 5.4 mmol, 25%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09115107B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-829ffae48875415885e90e2c4f24eee8 |
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| Source note | uspto-grants-2015_08 |
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