HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonamide → (R)-1-(3-fluorophenyl)-2-hydroxypropan-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonamide | HCID 72879 | — |
| Reactant | 1,4-Bis(dihydroquinidine)phthalazine | HCID 11217202 | — |
| Reactant | (Z)-tert-Butyl(1-(3-fluorophenyl)prop-1-enyloxy)dimethylsilane | HCID 46837928 | — |
| Solvent | 2-Methylpropan-2-ol--water (1/1) | HCID 71401949 | — |
| Product | (R)-1-(3-fluorophenyl)-2-hydroxypropan-1-one | HCID 46838072 | 87.2% |
Reaction Steps
Compound 10c was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(3-fluorophenyl)prop-1-enyloxy)dimethylsilane, (9c, 8.0 g, 0.030 mol), AD-mix-β (42.1 g), and CH3SO2NH2 (2.90 g, 0.0301 mol) in tert-butyl alcohol-water (120 mL:120 mL). The reaction was quenched with sodium sulfite (30.1 g). After purification, 4.4 g (87%) of the desired product 10c was isolated: [α]20D +58.1° (c 3.2, CHCl3); 1H NMR (CDCl3) δ 7.74-7.59 (m, 2H), 7.54-7.45 (m, 1H), 7.37-7.28 (m, 1H), 5.19-5.07 (m, 1H), 1.76 (d, 1H, J=6.3 Hz), 1.46 (d, 3H, J=6.9 Hz); 13C NMR (CDCl3) δ 201.6, 164.9, 131.0, (d), 124.7, 121.3 (d), 115.8 (d), 69.9, 22.4. C9H9FO2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08906908B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-f5bb6c92780d4532858b0eebd358879b |
| Source note | uspto-grants-2014_12 |