3-Benzyloxy-4-dimethylaminoestra-1,3,5(10)-trien-17-one → HCID 54174043, compound

HRID 1003195Notes

Reaction equation

HRID 1003195 reaction equation
C([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[C:10]=1[N:28]([CH3:30])[CH3:29])C1C=CC=CC=1>C1COCC1.[Pd]>[CH3:30][N:28]([CH3:29])[C:10]1[C:11]2[CH2:12][CH2:13][C@@H:14]3[C@@H:23]([C:24]=2[CH:25]=[CH:26][C:9]=1[OH:8])[CH2:22][CH2:21][C@@:19]1([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]1=[O:27]

Participants

4

Reactant 1

HCID 693344893-Benzyloxy-4-dimethylaminoestra-1,3,5(10)-trien-17-one

Product 1

HCID 54174043HCID 54174043, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyloxy-4-dimethylaminoestra-1,3,5(10)-trien-17-one (86, 0.271 g, 0.67 mmol) in THF (10 mL) was added 10% palladium on carbon (0.200 g). The reaction mixture was stirred for 1 h under a hydrogen atmosphere at room temperature. After the catalyst was filtered, the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (5:1→3:1, v/v) to afford 0.171 g of 87 (81% yield) mp: 155-156° C.

Workup

  1. filtrationAfter the catalyst was filtered
  2. customthe solvent was evaporated at reduced pressure
  3. customThe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-c0240dc9cc234654b227b6aa4c6c1c2f
Source dataset
uspto-grants-2000_04
Patent number
US06046186

Reaction notes

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