HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (R)-4-(4-((4'-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | (R)-ethyl 4-(4-((4'-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoate | HCID 56650671 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (R)-4-(4-((4'-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoic acid | HCID 58080224 | 79% |
Reaction Steps
A solution of (R)-ethyl 4-(4-((4′-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoate (INTERMEDIATE 11A (First Eluting Compound), 5.37 g, 11.93 mmol) in THF (160 ml), water (40 ml), and methanol (40 ml) was stirred at 50° C. overnight. The volatiles were removed under reduced pressure and the resulting residue was diluted with water (100 ml). The pH of the solution was adjusted to ˜5 with 1N aq. HCl (35 ml) promoting the formation of a precipitate. The white solid was collected via filtration and washed with water (˜150 ml). The filter cake was dried overnight under high vacuum at 50° C. to provide the title product (4.0 g, yield: 79%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09018381B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-0151467805d641c89b0a4f151834e5ca |
| Source note | uspto-grants-2015_04 |