HCID 12106154, compound → HCID 12106155, compound

HRID 2418139Notes

Reaction equation

HRID 2418139 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C:9](=[O:29])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[C@@H:12]3[CH2:28][C@@H:13]3[C:14]32[O:27][CH2:26][CH2:25][O:24]3)[CH2:6]1)(=[O:3])[CH3:2].C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>O1CCCC1.C(OCC)C>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C@H:9]([OH:29])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[C@@H:12]3[CH2:28][C@@H:13]3[C:14]32[O:27][CH2:26][CH2:25][O:24]3)[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 12106154HCID 12106154, compoundHCID 16684435Lithium tritertbutoxyaluminohydride

Product 1

HCID 12106155HCID 12106155, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

31 g of 3β-acetoxy-17,17-ethylenedioxy-15β,16β-methylene-5-androsten-7-one was reacted at room temperature within 1.5 hours in 310 ml of tetrahydrofuran with 31 g of lithium tri-tert.-butoxyaluminohydride. The reaction solution was diluted with diethyl ether, washed with potassium-sodium tartrate solution and water, dried, and evaporated. The residue was chromatographed on silica gel, thus obtaining 24.3 g 3β-acetoxy-17,17-ethylenedioxy-15β,16β-methylene-5-androsten-7β-ol, mp 199.5°-200° C. (acetone).

Workup

  1. washwashed with potassium-sodium tartrate solution and water
  2. customdried
  3. customevaporated
  4. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-9b1b2377181a4c028a8fd50568c94c34
Source dataset
uspto-grants-1984_09
Patent number
US04472310

Reaction notes

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