Tributylphosphine → Ethyl 3-(4-{[(1S)-1-(6-bromo-2-pyridinyl)pentyl]oxy}-2-methylphenyl)propanoate

HRID 1391778

Reaktionsgleichung

Reaktionsgleichung von HRID 1391778
[Br:1][C:2]1[N:7]=[C:6]([C@H:8]([OH:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1.O[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([CH3:28])[CH:16]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.CCCCP(CCCC)CCCC>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([C@@H:8]([O:13][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([CH3:28])[CH:16]=2)[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 21986481Ethyl 3-(4-hydroxy-2-methylphenyl)propanoateHCID 86604659(1R)-1-(6-Bromo-2-pyridinyl)-1-pentanol

Produkt 1

HCID 58629903Ethyl 3-(4-{[(1S)-1-(6-bromo-2-pyridinyl)pentyl]oxy}-2-methylphenyl)propanoateAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring solution of (1R)-1-(6-bromo-2-pyridinyl)-1-pentanol (261 mg, 1.07 mmol) and ethyl 3-(4-hydroxy-2-methylphenyl)propanoate (329 mg, 1.58 mmol) in THF (13 mL) at 0° C. under nitrogen was added ADDP (531 mg, 2.10 mmol) followed by tri-N-butylphosphine (0.525 mL, 2.10 mmol) drop-wise. The resulting mixture was then stirred with slow warming to ambient temperature over 15 h. The reaction mixture was then concentrated under vaccum and the solid residue purified directly by SPE (silica, 10 g cartridge) with a pad of celite on the top, eluting with cyclohexane:EtOAc (gradient 100:1 to 20:1) to afford the title compound (350 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under vaccum
  2. customthe solid residue purified directly by SPE (silica, 10 g cartridge) with a pad of celite on the top
  3. washeluting with cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-8d68972fb3fb4690a8df30f74b29f2da
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07338960B2

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