Lithium tritertbutoxyaluminohydride → HCID 70506062, compound

HRID 2418144Notes

Reaction equation

HRID 2418144 reaction equation
[C:1]([O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[C@@H:17]3[CH2:30][C@@H:18]3[C:19]2=[O:29])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>O1CCCC1.CCOCC>[C:1]([O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[C@@H:17]3[CH2:30][C@@H:18]3[C@@H:19]2[OH:29])[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 16684435Lithium tritertbutoxyaluminohydrideHCID 70505471HCID 70505471, compound

Product 1

HCID 70506062HCID 70506062, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

6.4 g of 3β-benzoyloxy-15β,16β-methylene-5-androsten-17-one was stirred in 64 ml of tetrahydrofuran with 6.4 g of lithium tri-tert.-butoxyaluminohydride for 1 hour at room temperature. The solution was then diluted with ether, washed with 2N sulfuric acid and water, dried, and evaporated, yielding as the residue 6.5 g of 3β-benzoyloxy-15β,16β-methylene-5-androsten-17β-ol, used without further purification in the subsequent stage.

Workup

  1. washwashed with 2N sulfuric acid and water
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-746c15f045e344d3b0984b708e47b4b3
Source dataset
uspto-grants-1984_09
Patent number
US04472310

Reaction notes

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