2,4,6-Trimethylpyridine → HCID 15097998, compound
Reaction equation
S(O[C@H:12]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@:14]([OH:33])([C@H:15]([OH:32])[CH2:16][C@@H:17]3[C@@H:26]2[CH2:25][CH2:24][C@@:22]2([CH3:23])[C@H:18]3[CH2:19][CH2:20][C:21]2=[O:31])[CH2:13]1)(C1C=CC(C)=CC=1)(=O)=O.N1C(C)=CC(C)=CC=1C>>[OH:33][C@:14]12[CH2:13][CH:12]=[CH:29][CH2:28][C@:27]1([CH3:30])[C@@H:26]1[C@H:17]([C@H:18]3[C@@:22]([CH2:24][CH2:25]1)([CH3:23])[C:21](=[O:31])[CH2:20][CH2:19]3)[CH2:16][C@H:15]2[OH:32]Participants
Conditions
- Temperature
- 160 °C
Procedure
70 g (0.147 mol) of the above-obtained 3β-tosyloxy-5α,6β-dihydroxy-17-oxo-androstane are dissolved in 350 ml. of collidine and the reaction mixture is heated in a nitrogen atmosphere, under stirring for 1.5 hours in an oil bath of 160° C. The collidine is then distilled off under reduced pressure, the evaporation residue is triturated with 400 ml. of water, filtred and washed with 10% aqueous hydrochloric acid solution, then with water to remove the last traces of collidine. The so-obtained product is dried in vacuo over phosphorous pentoxide at 40° C, and may be purified, if desired, by mixing with a fivefold amount of diethyl ether. 45 g of 5α,6β-dihydroxy-17-oxo-androst-2-ene (90%) are obtained; m.p. 183°-186° C; [α]D25 = +81° (c = 1 in chloroform).
Workup
- distillationThe collidine is then distilled off under reduced pressure
- customthe evaporation residue is triturated with 400 ml
- washwashed with 10% aqueous hydrochloric acid solution
- customwith water to remove the last traces of collidine
- dry with materialThe so-obtained product is dried in vacuo over phosphorous pentoxide at 40° C
- custommay be purified
- additionby mixing with a fivefold amount of diethyl ether
Sources & evidence
- ORD record
- ord-58741b5d338f491a9f92b3f0a6c9f1cd
- Source dataset
- uspto-grants-1978_08
- Patent number
- US04110326
Reaction notes
Loading…