Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 67220437 | HCID 67220437 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 44624272 | HCID 44624272 | 69.2% |
Reaction Steps
To the stirred solution of ethyl 2-(7-(4-(methylsulfonyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (40 mg, 0.094 mmol) in dioxane was added 1M LiOH aqueous solution (0.47 mL, 0.47 mmol). The reaction mixture was stirred at room temperature for 24 h. The solvent was partly removed, diluted with water, and acidified with HCl solution. The pinkish solid was collected and dried to give the title compound (26 mg). LCMS m/z=400.4 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 2.04-2.08 (m, 1H), 2.35 (dd, J=16.0 and 9.0 Hz, 1H), 2.63-2.75 (m, 4H), 3.20 (s, 3H), 3.45-3.50 (m, 1H), 5.21 (s, 2H), 6.73 (dd, J=8.7 and 2.4 Hz, 1H), 6.92 (d, J=2.4 Hz, 1H), 7.20 (d, J=8.7 Hz, 1H), 7.71 (d, J=8.3 Hz, 2H), 7.92 (d, J=8.3 Hz, 2H), 10.47 (s, 1H), 12.18 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08580841B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-ef6e5e7d5a594d1481595533ba5e8e4c |
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| Source note | uspto-grants-2013_11 |
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