Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 86630047 | HCID 86630047 | — |
| Catalyst | Dichloronickel;hexahydrate | HCID 11791229 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68984879 | HCID 68984879 | 85.2% |
Reaction Steps
At 5° C., 5.56 g of nickel (II) chloride hexahydrate is added to a solution of 6.00 g of ethyl 3-{5-[(2,4-diisobutoxyphenyl)(hydroxyimino)methyl]-2-isobutoxyphenyl}propanoate in 60 ml of methanol. Then, 4.42 g of sodium borohydride is portionwise added over a period of one hour. Water is added to the reaction mixture, and then 6 mol/L hydrochloric acid is dropwise added and stirred at ambient temperature for 10 minutes. pH is adjusted to 9 with saturated aqueous solution of sodium bicarbonate, methylene chloride is added, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Thus, 4.97 g of ethyl 3-{5-[amino(2,4-diisobutoxyphenyl)methyl]-2-isobutoxyphenyl}propanoate is obtained as a brown oily product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07314888B1 |
|---|
| Source dataset | uspto-grants-2008_01 |
|---|
| ORD ID | ord-376e897819124946befbe4766e9a1ed3 |
|---|
| Source note | uspto-grants-2008_01 |
|---|