HCID 69589049, compound → HCID 69589498, compound

HRID 859873Notes

Reaction equation

HRID 859873 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]([OH:27])[C@@H:17]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][Br:39])[CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[Br:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][C@H:17]1[CH2:16][C@H:15]2[C@H:14]3[C@H:23]([CH2:22][CH2:21][C@:19]2([CH3:20])[C@H:18]1[OH:27])[C:24]1[CH:25]=[CH:26][C:9]([OH:8])=[CH:10][C:11]=1[CH2:12][CH2:13]3

Participants

4

Reactant 1

HCID 69589049HCID 69589049, compound

Product 1

HCID 69589498HCID 69589498, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of 3-benzyloxy-16β-(11′-bromoundecanyl)-1,3,5(10)-estratrien-17β-ol (step C, 300 mg, 0,50 mmol) and 10% Pd/C (150 mg) in dry THF (4 mL) was stirred under hydrogen atmospheric pressure for 3–6 h. The reaction was followed by TLC until completion. The insoluble material was filtered off with diethyl ether (70 mL) and the filtrate was concentrated to give the crude product. It was purified by flash chromatography (hexanes:acetone (4:1)) to give 225 mg (90%) of a white solid.

Workup

  1. filtrationThe insoluble material was filtered off with diethyl ether (70 mL)
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product
  4. customIt was purified by flash chromatography (hexanes:acetone (4:1))

Sources & evidence

ORD record
ord-8528c09abe014c46aad25ece3a7ada5c
Source dataset
uspto-grants-2006_12
Patent number
US07153844B2

Reaction notes

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