Réaction #947055

ord-8528c09abe014c46aad25ece3a7ada5c

Équation de réaction

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
Rendement 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
Rendement 90.0%

Réactifs

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

Réactifs

[Pd]
Pd/C

Solvants

C1CCOC1
THF

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07153844B2uspto-grants-2006_12