HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → N-(1-(5-amino-2-benzyloxyphenyl)-1-methylethyl)carbamic acid t-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | N-(1-(2-benzyloxy-5-nitrophenyl)-1-methylethyl)carbamic acid t-butyl ester | HCID 22981078 | — |
| Catalyst | Dichloronickel;hexahydrate | HCID 11791229 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | N-(1-(5-amino-2-benzyloxyphenyl)-1-methylethyl)carbamic acid t-butyl ester | HCID 22981125 | 94.3% |
Reaction Steps
To a mixture of the compound (100 mg) obtained in Example 565, nickel (II) chloride hexahydrate (123 mg) and methanol (6 ml), sodium borohydride (39 mg) was added. The reaction mixture was stirred at room temperature for 10 min; then, 2 N HCl was added and a saturated aqueous sodium bicarbonate solution and chloroform were also added. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:2) to give 87 mg of the titled compound (yield, 94%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06534546B1 |
| Source dataset | uspto-grants-2003_03 |
| ORD ID | ord-7f84a9a7e5e84b4aa5ba1b129490f017 |
| Source note | uspto-grants-2003_03 |