Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 86668210 | HCID 86668210 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 68108916 | HCID 68108916 | — |
Reaction Steps
Pyrrolidine (25 uL, 0.30 mmol) and acetic acid (17 uL, 0.30 mmol) were added to a solution of 5-formyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 66; 100 mg, 0.30 mmol) in DCE (5 ml). The solution was stirred for 4 hours at 50° C. then sodium triacetoxyborohydride (96 mg, 0.45 mmol) was added. The reaction was stirred overnight then quenched with NaHCO3 solution (7 ml) and extracted with dichloromethane (5 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give a yellow solid. The residue purified by MDAP to yield the title compound as an opaque solid. 34 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08778939B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-ec395945cc7c4f9986cf23710a99edcf |
|---|
| Source note | uspto-grants-2014_07 |
|---|