Pregna-1,4,20-trien-3-one → Pregna-1,4,20-trien-3-ol

HRID 2270512Notes

Reaction equation

HRID 2270512 reaction equation
[CH2:1]=[CH:2][C@@H:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([CH2:18][CH2:19]2)[C@:15]2([CH3:16])[C:10](=[CH:11][C:12](=[O:22])[CH:13]=[CH:14]2)[CH2:9][CH2:8]3)[CH2:5][CH2:4]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:1]=[CH:2][C@@H:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([CH2:18][CH2:19]2)[C@:15]2([CH3:16])[C:10](=[CH:11][CH:12]([OH:22])[CH:13]=[CH:14]2)[CH2:9][CH2:8]3)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 13034987Pregna-1,4,20-trien-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 54245759Pregna-1,4,20-trien-3-olYield 10%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pregna-1,4,20-trien-3-one (3, 0.26 g, 088 mmol) in 25 ml of anh. ether was reduced under argon atmosphere with lithium aluminum hydride (250.5 mg, 6.601 mmol) for 2 h and then quenched with 2.50 g of Glauber's salt. The resulting suspension was stirred 70 min., filtered, and washed twice with 50 ml portions of ether. After concentrating the combined filtrates under reduced pressure the residue was purified using preparative TLC (35% ethyl acetate/hexanes on alumina to give white needles (26.1 mg, 87.4 μmol, 10%) m.p. 98-128° C.

Workup

  1. customquenched with 2.50 g of Glauber's salt
  2. filtrationfiltered
  3. washwashed twice with 50 ml portions of ether
  4. concentrationAfter concentrating the combined filtrates under reduced pressure the residue
  5. customwas purified

Sources & evidence

ORD record
ord-f14e4bc4e40d4f729e4dc7b3f8137ff7
Source dataset
uspto-grants-2001_12
Patent number
US06331534B1

Reaction notes

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