HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium hydroxide, monohydrate → (+/-)-(E)-2-(7-bromo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | (+/-)-(E)-ethyl 2-(7-bromo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetate | HCID 44226472 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (+/-)-(E)-2-(7-bromo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetic acid | HCID 58295679 | 48.6% |
Reaction Steps
(±)-(E)-ethyl 2-(7-bromo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetate (13 mg, mmol) was dissolved in THF (0.4 mL) and MeOH (0.8 mL). A solution of LiOH.H2O (10 mg) in water (0.4 mL) was added. The mixture was stirred at rt for 5 d. The reaction mixture was submitted directly to preparative HPLC to afford (±)-(E)-2-(7-bromo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (6 mg, %) as a solid. LC-MS Method 1 tR=1.92, min, m/z=522, 524.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08383629B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-48ac65f1e3dd47f48cf3aa69561990e3 |
| Source note | uspto-grants-2013_02 |