Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 59180075 | HCID 59180075 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59180051 | HCID 59180051 | — |
Reaction Steps
The title compound was synthesized from methyl 4-(3-ethynylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.014 g, 0.050 mmol) and lithium hydroxide (0.021 g, 0.50 mmol in 0.5 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (1 mL) was used. The resulting product was purified by reverse phase HPLC, eluting with a gradient of 40-100% MeOH: water (with 0.1% formic acid) to afford the title compound: 2.8 mg, 21% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.04-2.13 (m, 1H), 2.48-2.59 (m, 1H), 2.59-2.66 (m, 2H), 2.76 (d, J=7.22 Hz, 2H), 3.22-3.29 (m, 1H), 3.41 (s, 1H), 6.30 (s, 1H), 7.18-7.22 (m, 1H), 7.25 (t, J=7.81 Hz, 1H), 7.28-7.30 (m, 1H), 7.31 (s, 1H); LCMS (ESI−) 264.2 (M−H); HPLC (UV=96.60%), (ELSD=100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07902252B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-8146b1bcf12e4d15ab6de60493d1f25d |
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| Source note | uspto-grants-2011_03 |
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