3beta-Acetoxy-5-pregnene-20-one → HCID 54019415, compound

HRID 963168Notes

Reaction equation

HRID 963168 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([C@@H:6]1[C@@:10]2([CH3:28])[CH2:11][CH2:12][C@@H:13]3[C@@:18]4([CH3:27])[CH2:19][CH2:20][C@H:21]([O:23][C:24]([CH3:26])=[O:25])[CH2:22][C:17]4=[CH:16][CH2:15][C@H:14]3[C@@H:9]2[CH2:8][CH2:7]1)=[O:5]>C(O)C.C(Cl)Cl>[C:24]([O:23][CH:21]1[CH2:20][CH2:19][C@@:18]2([CH3:27])[C:17](=[CH:16][CH2:15][C@@H:14]3[C@@H:13]2[CH2:12][CH2:11][C@@:10]2([CH3:28])[C@H:9]3[CH2:8][CH2:7][C@@H:6]2[CH:4]([OH:5])[CH3:3])[CH2:22]1)(=[O:25])[CH3:26]

Participants

5

Reactant 2

HCID 27237223beta-Acetoxy-5-pregnene-20-oneHCID 4311764Sodium borohydride2×

Product 1

HCID 54019415HCID 54019415, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

Sodium borohydride (21 gm) was added to a solution of pregnenolone acetate (100 g, 0.28 mol) in absolute ethanol (1 L) and methylene chloride (0.4 L) at -10° C. After stirring overnight at 4° C., another amount of sodium borohydride (10.5 gm) was added and the reaction stirred at room temperature overnight. The reaction mixture was quenched by pouring into 5% sodium phosphate monobasic (2 L) and extracted with methylene chloride. The organic extracts were dried over anhydrous magnesium sulfate and filtered through a pad of anhydrous sodium sulfate. The solvent was removed by rotoevaporation to give the title compound.

Workup

  1. stirringthe reaction stirred at room temperature overnight
  2. customThe reaction mixture was quenched
  3. additionby pouring into 5% sodium phosphate monobasic (2 L)
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered through a pad of anhydrous sodium sulfate
  7. customThe solvent was removed by rotoevaporation

Sources & evidence

ORD record
ord-2eabb844376041b4b5d4a7b74d1d078b
Source dataset
uspto-grants-1998_06
Patent number
US05763361

Reaction notes

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