Potassium sodium tartarate → 3,17-Bis(ethylenedioxy)-16-fluoro-5-hydroxy-1beta-methyl-7-methylenandrostane

HRID 621624Notes

Reaction equation

HRID 621624 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[CH2:28][O:27][CH:26]2[CH:9]([CH2:10][C:11]34[O:37][C@H:12]3[C:13](=[CH2:36])[C@@H:14]3[C@@H:23]([C@@:24]4([CH3:30])[C@@H:25]2[CH3:29])[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][C@:17]3([F:35])[O:34][CH2:33][CH2:32][O:31][CH:18]32)[O:8]1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)C.O1CCCC1>[CH2:7]1[CH2:28][O:27][CH:26]2[CH:9]([CH2:10][C:11]3([OH:37])[C@:24]([CH3:30])([C@@H:25]2[CH3:29])[C@@H:23]2[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]2)([CH3:20])[CH:18]2[O:31][CH2:32][CH2:33][O:34][C:17]2([F:35])[CH2:16]4)[C:13](=[CH2:36])[CH2:12]3)[O:8]1

Participants

6

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 867429553,17-Bis(ethylenedioxy)-5,6alpha-epoxy-16alpha-fluoro-1beta-methyl-7-methylenandrostane

Product 1

HCID 867429563,17-Bis(ethylenedioxy)-16-fluoro-5-hydroxy-1beta-methyl-7-methylenandrostane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium aluminium hydride (38 mg) in diethylether (10 ml) is added gradually a solution of 3,17-bis(ethylenedioxy)-5,6α-epoxy-16α-fluoro-1β-methyl-7-methylenandrostane (431 mg) in tetrahydrofuran (10 ml). The resulting mixture is stirred at 20°-25° C. for a period of about 18 hrs after which an aqueous solution of potassium sodium tartrate is added. The mixture is filtered and concentrated to a small volume under reduced pressure. The concentrate is taken up in diethyl ether and washed well with water. The ether solution is dried over magnesium sulfate, filtered and the ether removed under vacuum to yield crude 3,17-bis(ethylenedioxy)-16-fluoro-5-hydroxy-1β-methyl-7-methylenandrostane. This intermediate is dissolved in a 2:1 mixture of acetic acid and water (5 ml) and the solution heated for 6 hrs at 40°-50° C. Then water is added and the product extracted with ethyl acetate.

Workup

  1. additionis added
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated to a small volume under reduced pressure
  4. washwashed well with water
  5. dry with materialThe ether solution is dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe ether removed under vacuum

Sources & evidence

ORD record
ord-a153d99df9df4fe4a9bed6f3732bb309
Source dataset
uspto-grants-1989_04
Patent number
US04824830

Reaction notes

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