HCID 15293266, compound → HCID 86749168, compound

HRID 863741Notes

Reaction equation

HRID 863741 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][CH2:28][CH2:29][O:30][C:31](=[O:48])[CH2:32][CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([N:41]([CH2:45][CH2:46][Cl:47])[CH2:42][CH2:43][Cl:44])=[CH:37][CH:36]=3)[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)C1C=CC=CC=1>[Pd].O1CCOCC1>[OH: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][CH2:28][CH2:29][O:30][C:31](=[O:48])[CH2:32][CH2:33][CH2:34][C:35]3[CH:36]=[CH:37][C:38]([N:41]([CH2:42][CH2:43][Cl:44])[CH2:45][CH2:46][Cl:47])=[CH:39][CH:40]=3)[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1

Participants

4

Reactant 1

HCID 15293266HCID 15293266, compound

Product 1

HCID 86749168HCID 86749168, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

10% palladium on carbon (320.7 mg) was placed into an eggplant type flask (100 ml), followed by dropwise addition of 1,4-dioxane (15 ml) at 0° C. To this mixture was added a 1, 4-dioxane (15 ml) solution of 1-[3-benzyloxy-1,3,5 (10)-estratriene-17β-oxy]-2-[4-[p-[bis (2-chloroethyl) amino]phenyl]-butyryloxy]ethane (I-5) dropwise at 0° C. The mixture was heated to room temperature and stirred under hydrogen gas for one hour. The reaction mixture was filtered through filter paper while washing with 1,4-dioxane, and the filtrate was concentrated under reduced pressure to produce an oily substance (0.27 g). It was purified by silica gel chromatography (hexane/ethyl acetate =3:1) to obtain 1-[3-hydroxy-1,3,5 (10)-estratriene-17β-oxy]-2-[4-[p-[bis (2-chloroethyl) amino]phenyl]butyryloxy]ethane (0.26 g) (Rf: 0.25, hexane/ethyl acetate=3:1) as oily substance.

Workup

  1. filtrationThe reaction mixture was filtered
  2. filtrationthrough filter paper
  3. washwhile washing with 1,4-dioxane
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto produce an oily substance (0.27 g)
  6. customIt was purified by silica gel chromatography (hexane/ethyl acetate =3:1)

Sources & evidence

ORD record
ord-e9b2b7fec9f948a891e761b73e50dd6e
Source dataset
uspto-grants-1996_10
Patent number
US05561125

Reaction notes

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