Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | HCID 67975561 | HCID 67975561 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67975730 | HCID 67975730 | 80% |
Reaction Steps
To a solution of 3-[1-dimethylamino-meth-(Z)-ylidene]-2-oxo-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]pyrrole-1-carboxylic acid tert-butyl ester E1 (190 mg, 0.579 mmol) in tetrahydrofurane (2 mL) was added hydrogen chloride (1M, 0.87 mL). The solution was stirred at room temperature for 3 h. The solution was diluted with ethyl acetate and washed with water, brine, dried and concentrated. The residue was triturated with ethyl acetate to give 3-[1-Hydroxy-meth-(Z)-ylidene]-2-oxo-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]pyrrole-1-carboxylic acid tert-butyl ester D1 (White powder, 140 mg, 80%). C17H19NO4; MW: 301.35; LCMS (method A) RT 1.72 min; ES: 302 (MK), 246; 1H NMR (400 MHz, DMSO-d6) δ 11.04 (1H, s), 7.54 (1H, d), 7.42 (1H, d), 7.13-7.31 (3H, m), 5.59 (1H, d), 3.70 (1H, m), 3.22 (1H, dd), 3.15 (1H, dd), 1.53 (10H, s) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08946280B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-3a7136c4f3c3450eaf0e4a017b6c388a |
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| Source note | uspto-grants-2015_02 |
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