HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetonitrile → Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[2-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- | HCID 85083 | — |
| Reactant | HCID 58545558 | HCID 58545558 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[2-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester | HCID 66620078 | 61% |
Reaction Steps
Crude 2-Bromo-1-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-ethanone (2.48 mmol assuming complete conversion from starting material) was treated with Boc-proline and MeCN (25 mL). Triethylamine was added and the solution was stirred at RT for 1 h then concentrated. The crude residue was purified by silica column chromatography (14% to 35% EtOAc/Hex) to afford the title compound (595 mg, 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08669234B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-aa878042c1e948488442c527bf1b6bd1 |
| Source note | uspto-grants-2014_03 |