Water → HCID 86738156, compound

HRID 1659835Notes

Reaction equation

[O:1]1[C@H:3]2[C:4](=[O:25])[CH:5]=[C:6]3[C@:22]([CH3:23])([C@@H:2]12)[C@@H:21]1[C@H:9]([C@H:10]2[C@:18]([CH3:24])([CH2:19][CH2:20]1)[C@@H:13]([C@H:14]([CH3:17])[CH2:15][OH:16])[CH2:12][CH2:11]2)[CH:8]=[CH:7]3.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:38][O:39][C:40]([CH3:42])=[CH2:41]>C1(C)C=CC=CC=1.C(N(CC)CC)C.N1C=CC=CC=1>[O:1]1[C@H:3]2[C:4](=[O:25])[CH:5]=[C:6]3[C@:22]([CH3:23])([C@@H:2]12)[C@@H:21]1[C@H:9]([C@H:10]2[C@:18]([CH3:24])([CH2:19][CH2:20]1)[C@@H:13]([C@H:14]([CH3:17])[CH2:15][O:16][C:40]([O:39][CH3:38])([CH3:42])[CH3:41])[CH2:12][CH2:11]2)[CH:8]=[CH:7]3

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3.42 g (10 mmol) of (20S)-1α,2α-epoxy-21-hydroxy-20-methyl-pregna-4,6-dien-3-one in 100 ml of toluene is concentrated to 50 ml in a water-jet vacuum. The resulting suspension is treated at 0° C. with 2 ml of a suspension prepared from 50 ml of toluene, 0.172 g of p-toluenesulphonic acid and 0.2 ml of pyridine. Thereafter 3 ml of isopropenyl methyl ether are added and the resulting mixture is stirred at 0° C. for 3 hours. After the addition of 1 ml of triethylamine, the mixture is concentrated at 30° C./11 Torr. The crystalline residue is dissolved in a small amount of methylene chloride containing 0.1% triethylamine and treated with ether to give 2.91 g (70%) of (20S)-1α,2α-epoxy-21-(1-methoxy-1-methylethoxy)-20 -methyl-pregna-4,6-dien-3-one of melting point 150°-151° C.; [ α]D25 =+185.8° C. (c=1.0 in chloroform containing 0.1% triethylamine).

Workup

concentrationthe mixture is concentrated at 30° C./11 Torr
dissolutionThe crystalline residue is dissolved in a small amount of methylene chloride containing 0.1% triethylamine
additiontreated with ether

Sources & evidence

ORD record: ord-9b861be1e09c46ff9100a14e4616ba75
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04305881

Reaction notes

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