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

HRID 2258003Notes

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

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 (97.6 gm, 87% yield).

Workup

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

Sources & evidence

ORD record: ord-e27f9a180d004ccfa664235486af0a42
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05658922

Reaction notes

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