Reaktion #947055

ord-8528c09abe014c46aad25ece3a7ada5c

Reaktionsgleichung

C[C@]12CC[C@@H]3c4ccc(OCc5ccccc5)cc4CC[C@H]3[C@@H]1C[C@H](CCCCCCCCCCCBr)[C@@H]2O
3-benzyloxy-16β-(11′-bromoundecanyl)-1,3,5(10)-estratrien-17β-ol
→
C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1C[C@H](CCCCCCCCCCCBr)[C@@H]2O
white solid
Ausbeute 90.0%
C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1C[C@H](CCCCCCCCCCCBr)[C@@H]2O
16β-(11′-bromoundecanyl)-1,3,5(10)-estratrien-3,17β-diol
Ausbeute 90.0%

Edukte

C[C@]12CC[C@@H]3c4ccc(OCc5ccccc5)cc4CC[C@H]3[C@@H]1C[C@H](CCCCCCCCCCCBr)[C@@H]2O
3-benzyloxy-16β-(11′-bromoundecanyl)-1,3,5(10)-estratrien-17β-ol

Reagenzien

[Pd]
Pd/C

Lösungsmittel

C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe insoluble material was filtered off with diethyl ether (70 mL)
  2. 2
    Einengenthe filtrate was concentrated
  3. 3
    Sonstigeto give the crude product
  4. 4
    SonstigeIt was purified by flash chromatography (hexanes:acetone (4:1))

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07153844B2uspto-grants-2006_12