HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,8-Diazabicyclo(5.4.0)undec-7-ene → 2,3-diethyl (2R,3R)-oxirane-2,3-dicarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | diethyl (2S,3S)-oxirane-2,3-dicarboxylate | HCID 7021072 | — |
| Reactant | Diethyl (2S,3S)-2-bromo-3-hydroxysuccinate | HCID 10901630 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | 2,3-diethyl (2R,3R)-oxirane-2,3-dicarboxylate | HCID 2733646 | 74.8% |
Reaction Steps
Followed general procedure for 3a using the following quantities: 2b (34.6 g, 129 mmol): Et2O (100 ml); DBU (29.4 g, 193 mmol, in Et2O [50 ml]); yielded 3b as a colorless oil (18.1 g, 74.8%). 1H NMR (CDCl3, 400 MHz): δ 4.36-4.22 (m, 4H); 3.67 (s, 2H); 1.35-1.31 (t, 6H). 13C NMR (CDCl3, 100 MHz): 166.75, 62.21, 52.01, 14.01.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09403843B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-fa2dbd3d26774a96ad5bb6d6135f93f6 |
| Source note | uspto-grants-2016_08 |