methyl (E,E)-5-(3beta,14beta-dihydroxy-5beta-androstane-17beta-yl)-2,4-pentadienoate → (E,E)-5-(3beta,14beta-dihydroxy-5beta-androstane-17beta-yl)-2,4-pentadien-1-ol

HRID 1080633Notes

Reaction equation

HRID 1080633 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@:8]3([OH:29])[CH2:9][CH2:10][C@@H:11]2/[CH:21]=[CH:22]/[CH:23]=[CH:24]/[C:25](OC)=[O:26])[CH2:3]1>O1CCCC1.[AlH](CC(C)C)CC(C)C.CCCCCC>[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@:8]3([OH:29])[CH2:9][CH2:10][C@@H:11]2/[CH:21]=[CH:22]/[CH:23]=[CH:24]/[CH2:25][OH:26])[CH2:3]1

Participants

5

Reactant 1

HCID 86750052methyl (E,E)-5-(3beta,14beta-dihydroxy-5beta-androstane-17beta-yl)-2,4-pentadienoate

Product 1

HCID 10738195(E,E)-5-(3beta,14beta-dihydroxy-5beta-androstane-17beta-yl)-2,4-pentadien-1-olYield 66.2%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 14487Diisobutylaluminum hydrideSolvent

Procedure

To a solution of 7.95 g of methyl (E,E)-5-(3β,14β-dihydroxy-5β-androstane-17β-yl)-2,4-pentadienoate (Boutagy J. and Thomas R., Aust. J. Pharm. Chem., 1972, NS1, 67) in 390 ml of dry tetrahydrofuran, 133 ml of 1M i-Bu2AlH in hexane were added dropwise under nitrogen at -78° C. After 2 hrs the reaction was quenched with aqueous sodium sulfate (63 g in 390 ml of water) and stirred at room temperature overnight. The mixture was then filtered through Celite and washed with ethyl acetate. The organic solution was dried over anhydrous sodium sulfate and evaporated to dryness to give 4.90 g of (E,E)-5-(3β,14β-dihydroxy-5β-androstane-17β-yl)-2,4-pentadien-1-ol as an off-white solid.

Workup

  1. customAfter 2 hrs the reaction was quenched with aqueous sodium sulfate (63 g in 390 ml of water)
  2. filtrationThe mixture was then filtered through Celite
  3. washwashed with ethyl acetate
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-c362c882dc0f42b3862e2979bea4c92c
Source dataset
uspto-grants-1996_12
Patent number
US05583127

Reaction notes

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