HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methoxypropene → 3-(t-Butyloxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-vinyloxazolidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methoxypropene | HCID 8300 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4(S)-t-Butyloxycarbonylamino-5-cyclohexyl-3(R,S)hydroxy-1-pentene | HCID 13891106 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-(t-Butyloxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-vinyloxazolidine | HCID 22418893 | 124.9% |
Reaction Steps
The procedure of S. Thaisrivong (J. Med. Chem. 1987, 30, 976) was employed. A solution of 40 g of the resultant compound of Example 17 and 102 g of 2-methoxypropene in 250 ml of dichloromethane was stirred at room temperature. Solid pyridinium p-toluenesulfonate (PPTS) (177 g) was added slowly to the reaction mixture. After addition was complete, the reaction was stirred for 1 h and neutralized by addition of solid sodium bicarbonate. The solids were filtered and the filtrate was concentrated. Flash chromatography on silica gel gave 57 g of the desired compound. IR (CDCl3) 1690 (C=O carbamate) cm-1 ; 1H NMR (CDCl3) δ5.95 (m,1H), 5.32 (m,1H), 5.20 (dt,1H), 4.27 (dd,1H), 1.47 (s,9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05268374 |
| Source dataset | uspto-grants-1993_12 |
| ORD ID | ord-e9253dcc6f054f59acf78884cb489021 |
| Source note | uspto-grants-1993_12 |