Sodium borohydride → HCID 66652033, compound

HRID 418971Notes

Reaction equation

HRID 418971 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[CH:12]([C:16](=[O:18])[CH3:17])[CH:11]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH:10]1[CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9]1.[BH4-].[Na+]>C(O)C>[OH:18][CH:16]([CH:12]1[C:13]2[CH:14]=[CH:15][C:2]([OH:1])=[CH:3][C:4]=2[CH:5]2[CH:10]([CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:11]1[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH3:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66651989HCID 66651989, compound

Product 1

HCID 66652033HCID 66652033, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 1-[6-hydroxy-10-(4-hydroxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-ethanone (0.027 g, 0.08 mmol), NaBH4 (0.010 g, 0.24 mmol), and ethanol (4 mL), and reflux under nitrogen atmosphere. After 72 hours, cool the reaction to room temperature, concentrate, and add ethyl acetate. Wash with sat ammonium chloride solution (aq), then brine, and purify using reverse phase chromatography (5% to 95% 0.001% TFA buffer in acetonitrile/water) to yield the titled compound (0.003 g, 11%) as a white solid. 1H NMR (d-methanol): 7.62 (d, 1H, J=8.4 Hz), 7.15 (m, 2H), 6.84 (s, 1H), 6.78 (m, 2H), 6.64 (m, 1H), 3.94 (m, 1H), 3.49 (d, 1H, J=11.5 Hz), 3.33 (m, 1H), 3.13 (s, 1H), 2.91 (dd, 1H, J=11.5, 3.5 Hz), 2.47 (m, 1H), 1.86 (m, 1H), 1.68 (m, 1H), 1.52 (m, 1H), 1.30 (m, 3H), 1.05 (m, 4H), 0.83 (d, 2H, J=6.2 Hz); MS m/z 337 (M−1).

Workup

  1. temperaturecool
  2. customthe reaction to room temperature
  3. concentrationconcentrate
  4. additionadd ethyl acetate
  5. washWash with sat ammonium chloride solution (aq)
  6. custombrine, and purify

Sources & evidence

ORD record
ord-f53d068e8fce405581e4f559a84afa67
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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