Triphenylphosphine → ethyl ((1S)-5-{2-[(2,6-dimethyl-3-pyridinyl)oxy]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate

HRID 603446

Reaktionsgleichung

Reaktionsgleichung von HRID 603446
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9][CH2:8]2.[CH3:20][C:21]1[C:26](O)=[CH:25][CH:24]=[C:23]([CH3:28])[N:22]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH3:20][C:21]1[C:26]([O:1][CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[C@H:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9][CH2:8]3)=[CH:25][CH:24]=[C:23]([CH3:28])[N:22]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 707322,6-Dimethyl-3-pyridinolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 59300449ethyl [(1S)-5-(2-hydroxyethoxy)-2,3-dihydro-1H-inden-1-yl]acetate

Produkt 1

HCID 59300516ethyl ((1S)-5-{2-[(2,6-dimethyl-3-pyridinyl)oxy]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl [(1S)-5-(2-hydroxyethoxy)-2,3-dihydro-1H-inden-1-yl]acetate (Example 249, 50.0 mg, 0.19 mmol) and 2,6-dimethylpyridin-3-ol (46.6 mg, 0.38 mmol) in THF (1.5 mL) were added PPh3 (99.2 mg, 0.38 mmol) and ADDP (95.5 mg, 0.38 mmol). The reaction mixture was vigorously stirred at rt for 24 h, and then directly applied to a silica gel column for purification (1:1 hexanes/EtOAc) to give the product (58.9 mg, 84%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.29 (t, 3H) 1.72-1.81 (m, 1H), 2.36-2.2.44 (m, 2H), 2.45 (s, 3H), 2.47 (s, 3H), 2.73 (dd, 1H) 2.82-2.92 (m, 2H), 3.52-3.56 (m, 1H) 4.19 (q, 2H), 4.26-4.33 (m, 4H), 6.75 (d, 1H), 6.82 (s, 1H) 6.92 (d, 1H), 7.05 (d, 1H), 7.08 (d, 1H).

Aufarbeitung

  1. customdirectly applied to a silica gel column for purification (1:1 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-c4f2660a6f224899a0f40533804a2b6a
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906653B2

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