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

HRID 23361Notes

Reaction equation

HRID 23361 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-diol

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 (3×). The organic fractions were washed with water (2×), brine (1×), 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 (3×)
  6. washThe organic fractions were washed with water (2×), brine (1×)
  7. filtrationfiltered through sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-8495cdd51900489598f5fe670caee2fa
Source dataset
uspto-grants-2005_02
Patent number
US06852710B2

Reaction notes

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