1,4-Dioxane → HCID 68132020, compound

HRID 1579433Notes

Reaction equation

HRID 1579433 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7](C=C[C:10]4[C@:15]3([CH3:16])[CH:14]=[CH:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].[O:22]1[CH2:27][CH2:26][O:25]CC1>[Os](=O)(=O)(=O)=O.N1C=CC=CC=1>[OH:22][C@H:27]1[C:14]2[C@:15]([CH3:16])([CH:10]=[CH:11][C:12](=[O:20])[CH:13]=2)[C@@H:17]2[C@H:7]([C@H:6]3[C@@:2]([CH2:19][CH2:18]2)([CH3:1])[C:3](=[O:21])[CH2:4][CH2:5]3)[C@H:26]1[OH:25]

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 104880Androsta-1,4,6-triene-3,17-dione

Product 1

HCID 68132020HCID 68132020, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 1049PyridineSolvent

Procedure

To 0.83 g. of 1,4,6-androstatriene-3,17-dione in 15 ml. of dioxane and 0.83 ml. of pyridine add 0.75 g. of osmium tetroxide. Stir the reaction mixture under an atmosphere of nitrogen at room temperature in the absence of light for two days. Isolate the resultant product in a manner similar to that described in Example 1B. Purify by chromatographing on thin layer plates developing with ethyl acetate-chloroform-methanol (4.5:4.5:1). Combine like fractions, elute with ethyl acetate, and evaporate the eluate to a residue comprising 6β,7β-dihydroxy-1,4-androstadiene-3,17-dione. Yield=445 mg. (48% theory). Further purify by recrystallization from methanol; [α]D26° +66.7° (acetone); λmaxmethanol 244 nm (γ=15,300); n.m.r. (dmso-d6 /D2O) δ0.89 (C13 -CH3); 1.37 (C10 -CH3); 3.25(7α-H; d,d J10,3Hz); 4.24 (6α-H; d,J 3.5Hz); 6.11 (C4 -H; d,J 2Hz); 6.11 (C2 -H; d,d J10,2Hz); 7.18 (C1H; d,J 10Hz).

Sources & evidence

ORD record
ord-caf22752e7f045c08022d4dcd7b13fc1
Source dataset
uspto-grants-1976_01
Patent number
US03931167

Reaction notes

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