Benzyl Bromide → 1-(S)-Benzyloxymethyl-2-(S)-(3-fluorophenyl)-4-methylenecyclopentane

HRID 8778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 8778
[OH:1][CH2:2][C@@H:3]1[CH2:7][C:6](=[CH2:8])[CH2:5][C@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+]>CN(C=O)C.CCOCC>[CH2:16]([O:1][CH2:2][C@H:3]1[CH2:7][C:6](=[CH2:8])[CH2:5][C@@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 23548915(+)-trans-1-Hydroxymethyl-4-methylene-2-(3-fluorophenyl)cyclopentane

Produkt 1

HCID 235489111-(S)-Benzyloxymethyl-2-(S)-(3-fluorophenyl)-4-methylenecyclopentaneAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (+)-trans-1-hydroxymethyl-4-methylene-2-(3-fluorophenyl)cyclopentane (5.0 g, 26.5 mmol) from Example 1, Step C and benzyl bromide (4.7 mL, 40 mmol) in DMF (130 mL) was added 60% sodium hydride in mineral oil (0.77 g, 32 mmol). The reaction was stirred at room temperature for 24 h was then diluted with ether and slowly quenched into aq. sodium bicarbonate. After three ether extractions, the organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by FC (2–5% ethyl acetate in hexanes) to afford the title compound (7.1 g).

Aufarbeitung

  1. customslowly quenched into aq. sodium bicarbonate
  2. extractionAfter three ether extractions
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by FC (2–5% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f4f5c73c0baa450b83cabe4ac2020d77
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091211B2

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