Sodium borohydride → HCID 69913656, compound

HRID 353706Notes

Reaction equation

HRID 353706 reaction equation
[BH4-].[Na+].[CH2:3]([C@@H:5]1[CH2:22][C:21]2[CH2:20][C:19](=[O:23])[CH2:18][CH2:17][C:16]=2[C@@H:15]2[C@@H:6]1[C@H:7]1[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C@@H:10]([OH:24])[CH2:9][CH2:8]1)[CH3:4]>O1CCCC1.CO>[CH2:3]([C@@H:5]1[CH2:22][C:21]2[CH2:20][C@H:19]([OH:23])[CH2:18][CH2:17][C:16]=2[C@@H:15]2[C@@H:6]1[C@H:7]1[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C@@H:10]([OH:24])[CH2:9][CH2:8]1)[CH3:4].[CH2:3]([C@@H:5]1[CH2:22][C:21]2[CH2:20][C@@H:19]([OH:23])[CH2:18][CH2:17][C:16]=2[C@@H:15]2[C@@H:6]1[C@H:7]1[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C@@H:10]([OH:24])[CH2:9][CH2:8]1)[CH3:4]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 69913658HCID 69913658, compound

Product 2

HCID 69913656HCID 69913656, compoundHCID 69913704HCID 69913704, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.013 g) was added to a solution of (7α,17β)-7-ethyl-17-hydroxyestr-5(10)en-3-one (Example 2; 0.25 g) in a mixture of tetrahydrofuran (4.2 ml) and methanol (4.2 ml). The reaction mixture was stirred at room temperature for 2 h and then quenched with acetone. The mixture was poured into water and the product was extracted into ethyl acetate. The combined organic phases were washed with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. Column chromatography afforded (3α,7α,17β)-7-ethylestr-5(10)-ene-3,17-diol, m.p. 98-100° C., and (3β,7α,17β)-7-ethylestr-5(10)-ene-3,17-diol, m.p. 60-65° C.

Workup

  1. customquenched with acetone
  2. additionThe mixture was poured into water
  3. extractionthe product was extracted into ethyl acetate
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-41eee78ebbf5414485f3b37577516abe
Source dataset
uspto-grants-2004_06
Patent number
US06756366B1

Reaction notes

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