Acetic Acid → 2-Methoxyestra-1,3,5(10),14-tetraen-3,17beta-diol

HRID 1357476Notes

Reaction equation

HRID 1357476 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:25]C(=O)C)=[CH:5][C:6]2[CH2:7][CH2:8][C@@H:9]3[C@@H:18]([C:19]=2[CH:20]=1)[CH2:17][CH2:16][C@@:14]1([CH3:15])[C:10]3=[CH:11][CH:12]=[C:13]1[O:21]C(=O)C.[BH4-].[Na+].C(O)(=O)C>C(O)C.C1COCC1.C(O)C.O.O>[CH3:1][O:2][C:3]1[C:4]([OH:25])=[CH:5][C:6]2[CH2:7][CH2:8][C@@H:9]3[C@@H:18]([C:19]=2[CH:20]=1)[CH2:17][CH2:16][C@@:14]1([CH3:15])[C:10]3=[CH:11][CH2:12][C@@H:13]1[OH:21]

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 113265312-Methoxy-3,17-diacetoxyestra-1,3,5(10),14,16-pentaene

Product 1

HCID 98393052-Methoxyestra-1,3,5(10),14-tetraen-3,17beta-diolYield 55.7%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the diacetate (17) (0.08 g, 0.21 mmol) in ethanol (5 mL) and THF (3 mL) was cooled to 0° C. in an ice bath. A solution of sodium borohydride (0.05 g, 1.32 mmol) in ethanol/water (10:3, 5 mL) was cooled to 0° C. in an ice bath and added to the steroid solution. The reaction mixture was stirred at 0° C. for 1 h., then allowed to warm to room temperature and stirred overnight. After that time, the reaction was diluted with water (20 mL) and neutralized with glacial acetic acid. The organic solvents were removed in vacuo under a stream of nitrogen, the residue was diluted with water (50 mL) and extracted with methylene chloride (3x). The organic fractions were washed with water (2x), brine (1x), filtered through sodium sulfate, combined and concentrated in vacuo. The residue was triturated with ether to give the pure product (18) (0.035 g, 55.7%).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. customThe organic solvents were removed in vacuo under a stream of nitrogen
  4. additionthe residue was diluted with water (50 mL)
  5. extractionextracted with methylene chloride (3x)
  6. washThe organic fractions were washed with water (2x), brine (1x)
  7. filtrationfiltered through sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-25bbb2111826468e9e71bf9af1695717
Source dataset
uspto-grants-2003_07
Patent number
US06593321B2

Reaction notes

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