Sodium borohydride → HCID 69789988, compound

HRID 1815786Notes

Reaction equation

HRID 1815786 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C:11]3=[CH:12][CH2:13][C:14]2=[O:24])[CH2:6]1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C:11]3=[CH:12][CH2:13][C@@H:14]2[OH:24])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69283076HCID 69283076, compound2×

Product 1

HCID 69789988HCID 69789988, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-10 °C

Procedure

i)—A solution of (3β)-3-(acetyloxy)androsta-5,14-dien-17-one [Andre, A. F. St. et al, J. Am. Chem. Soc. 74, 5506 (1952); 42.9 g] in dry ethanol (429 ml) was cooled to −10° C. Sodium borohydride (1.51 g) in dry ethanol (33.5 ml) was added and the mixture was stirred at −10° C. for 7.5 h. Excess sodium borohydride was destroyed by careful addition of an aqueous solution of acetic acid (50%). The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate and concentrated. Column chromatography provided (3β,17β)-androsta-5,14-diene-3,17-diol 3-acetate (19.5 g).

Workup

  1. customExcess sodium borohydride was destroyed by careful addition of an aqueous solution of acetic acid (50%)
  2. extractionThe product was extracted into ethyl acetate
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-37c715f5172249818bca67b38e84cc0f
Source dataset
uspto-grants-2005_04
Patent number
US06881728B1

Reaction notes

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