Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | D-Leucine Methyl Ester Hydrochloride | HCID 11600782 | — |
| Reactant | Benzyl (1-formylcyclopropyl)carbamate | HCID 54500481 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67426229 | HCID 67426229 | 47% |
Reaction Steps
Methyl D-leucinate hydrochloride (2.73 g, 15.1 mmol), zinc chloride (2.8 g, 20.5 mmol), and sodium triacetoxyborohydride (9.16 g, 41.1 mmol) were added to a dichloromethane (200 ml) solution of benzyl (1-formylcyclopropyl)carbamate (3.0 g, 13.7 mmol) and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, the residue obtained was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution and saturated brine and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=2:1 (v/v)] to give the title compound (2.24 g, 47%) as a pale yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08404691B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-172bd77979f8483493de2ae9e2b43062 |
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| Source note | uspto-grants-2013_03 |
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