Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Hydroxyamine hydrochloride | HCID 443297 | — |
| Reactant | (R)-benzyl 1-cyanoethylcarbamate | HCID 10703364 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 140555601 | HCID 140555601 | 99.4% |
Reaction Steps
To a solution of benzyl [(1R)-1-cyanoethyl]carbamate (2.52 g, 12.3 mmol) in ethanol (30 ml) was added hydroxylamine hydrochloride salt (0.90 g, 13.0 mmol) and triethylamine (3.43 ml, 24.6 mmol) and the mixture heated to 75° C. After 16 h, the solution was concentrated and the residue was dissolved in 200 mL of dichloromethane. The mixture was washed with 100 mL of saturated aqueous sodium bicarbonate (2×) and brine (100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to give benzyl [(1R,2Z)-2-amino-2-(hydroxyimino)-1-methylethyl]carbamate (2.9 g). MS 238.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08598209B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-f9d8ca1838134210a5efb46b02f08d2a |
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| Source note | uspto-grants-2013_12 |
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