Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | (S)-2-(Boc-Amino)-N-methoxy-n-methylbutyramide | HCID 10422029 | — |
| Reactant | HCID 178420628 | HCID 178420628 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57577512 | HCID 57577512 | 94% |
Reaction Steps
A solution of tert-butyl {(1S)-1-[methoxy(methyl)carbamoyl]propyl}carbamate (14.3 g) in tetrahydrofuran (130 mL) was ice-cooled under a nitrogen atmosphere, and 1.0 mol/L-cyclopropylmagnesium bromide/tetrahydrofuran solution (300 mL) was added. The mixture was stirred at the same temperature for 4.5 hr, saturated aqueous ammonium chloride solution (300 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→16%) to give the title compound as a colorless oil (yield: 10.7 g, 94%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08420694B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-28d54e61c6f04162988eb1eefc5ddffb |
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| Source note | uspto-grants-2013_04 |
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