HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → HCID 67413948, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | HCID 15767265 | HCID 15767265 | — |
| Reactant | (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one | HCID 51066623 | — |
| Product | HCID 67413948 | HCID 67413948 | 27% |
Reaction Steps
The compound was prepared in a manner similar as to that described above using (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one, 4-cyclopentyl-cyclohexanol (1.5 g, 0.0090 mol), triphenylphosphine (2.6 g, 0.0099 mol), tetrahydrofuran (45 mL, 0.55 mol) and diisopropyl azodicarboxylate (2.0 g, 0.0099 mol) to give 895 mg of a 1.6 to 1 diasteromeric ratio of the desired compound as a yellow solid (27%). ESI-MS: 368 (M+H)+. 1H NMR (400 MHz, CDCl3) δ=7.80-7.63 (m, 3 H), 7.39 (dd, J=1.9, 8.7 Hz, 1 H), 7.22-7.08 (m, 2 H), 4.70-4.58 (br. s., 0.63 H), 4.43-4.36 (s, 2 H), 4.34-4.21 (tt, J=4.2, 6.5 Hz, 0.39 H), 2.04 (s, 2 H), 1.87-1.70 (m, 2 H), 1.65-0.77 (m, 17 H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08269043B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-78dc969e3d3f47b68768c18ea418d281 |
| Source note | uspto-grants-2012_09 |