Tetrahydrofuran → HCID 15292629, compound

HRID 1080638Notes

Reaction equation

HRID 1080638 reaction equation
[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@:8]3([OH:24])[CH2:9][CH2:10][C@@H:11]2[CH2:12][C:13]#N)[CH2:3]1.[O:25]1CCCC1>[AlH](CC(C)C)CC(C)C.CCCCCC>[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@:8]3([OH:24])[CH2:9][CH2:10][C@@H:11]2[CH2:12][CH:13]=[O:25])[CH2:3]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 10782753HCID 10782753, compound

Product 1

HCID 15292629HCID 15292629, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 14487Diisobutylaluminum hydrideSolvent

Procedure

To a solution of 8.50 g of 3β,14β-dihydroxy-5β-pregnane-21-nitrile in 500 ml of dry tetrahydrofuran, 105 ml of 1M i-Bu2AlH in hexane were added dropwise under nitrogen at 0° C. After 1 hr the reaction was quenched with aqueous citric acid (7.05 g in 32.5 ml of water) and stirred at room temperature for 1 hr. 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 6.05 g of the title compound (II-b) partially in the internal hemiacetal form, as a white foam.

Workup

  1. customAfter 1 hr the reaction was quenched with aqueous citric acid (7.05 g in 32.5 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-365ac41ade00464b9028a6fbb830a6bf
Source dataset
uspto-grants-1996_12
Patent number
US05583127

Reaction notes

Loading…