HCID 69334501, compound → HCID 53766333, compound

HRID 1003180Notes

Reaction equation

HRID 1003180 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@H:18]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[Si:28]([O:27][C@@H:18]1[CH2:17][CH2:16][C@H:15]2[C@H:14]3[C@H:23]([CH2:22][CH2:21][C@:19]12[CH3:20])[C:24]1[CH:25]=[CH:26][C:9]([OH:8])=[CH:10][C:11]=1[CH2:12][CH2:13]3)([C:31]([CH3:34])([CH3:32])[CH3:33])([CH3:30])[CH3:29]

Participants

4

Reactant 1

HCID 69334501HCID 69334501, compound

Product 1

HCID 53766333HCID 53766333, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyloxy-17α-tert-butyldimethylsilyloxyestra-1,3,5(10)-triene (50, 1.90 g, 4.0 mmol) in THF (30 mL) was added 10% palladium on carbon (0.500 g). The reaction mixture was stirred for 2 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 (10:1→5:1, v/v) to afford 1.45 g of 51 (94% yield) mp: 161-162° C. (silica gel) using n-hexane:EtOAc (10:1→5:1, v/v) to afford 1.45 g of 51 (94% yield) mp: 161-162° 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-c904f91c2a4d495885df37eba34b3e90
Source dataset
uspto-grants-2000_04
Patent number
US06046186

Reaction notes

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