ethyl (E)-3beta,14beta-dihydroxy-21-methyl-5beta-pregn-20-ene-21-carboxylate → (E)-21-hydroxymethyl-21-methyl-5beta-pregn-20-ene-3beta,14beta-diol

HRID 725261Notes

Reaction equation

HRID 725261 reaction equation
[OH:1][C@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@:8]3([OH:29])[CH2:9][CH2:10][C@@H:11]2/[CH:12]=[C:13](\[CH3:19])/[C:14](OCC)=[O:15])[CH2:3]1>O1CCCC1.[AlH](CC(C)C)CC(C)C.CCCCCC>[OH:15][CH2:14]/[C:13](/[CH3:19])=[CH:12]/[C@@H:11]1[C@:20]2([CH3:28])[C@@:8]([OH:29])([C@H:7]3[C@H:23]([CH2:22][CH2:21]2)[C@:24]2([CH3:27])[C@@H:4]([CH2:3][C@@H:2]([OH:1])[CH2:26][CH2:25]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1

Participants

5

Reactant 1

HCID 86751868ethyl (E)-3beta,14beta-dihydroxy-21-methyl-5beta-pregn-20-ene-21-carboxylate

Product 1

HCID 10690052(E)-21-hydroxymethyl-21-methyl-5beta-pregn-20-ene-3beta,14beta-diolYield 96.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 14487Diisobutylaluminum hydrideSolvent

Procedure

To a solution of 9.60 g of ethyl (E)-3β,14β-dihydroxy-21-methyl-5β-pregn-20-ene-21-carboxylate (Boutagy J. and Thomas R., Aust. J. Pharm, Chem., 1972, NS1, 67) in 370 ml of dry tetrahydrofuran, 104 ml of 1M i-Bu2AlH in hexane were added dropwise under nitrogen at -78° C. After 2 hrs the reaction was quenched with a solution of 46.0 g of sodium sulfate in 350 ml of water and stirred at room temperature for 2 hours. The mixture was then filtered through Celite and washed with methylene chloride. The organic layer was separated, dried over anhydrous sodium sulfate and evaporated to dryness to give 8.30 g of (E)-21-hydroxymethyl-21-methyl-5β-pregn-20-ene-3β,14β-diol as an off-white solid.

Workup

  1. customAfter 2 hrs the reaction was quenched with a solution of 46.0 g of sodium sulfate in 350 ml of water
  2. filtrationThe mixture was then filtered through Celite
  3. washwashed with methylene chloride
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-bfbd5c13ea4c4713b66cb7dd519caec8
Source dataset
uspto-grants-1998_01
Patent number
US05705662

Reaction notes

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