Peracetic Acid → tert-Butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

HRID 1666409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666409
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:17]=[C:18]([CH:33]=[CH:34][CH:35]=3)[CH:19]=[C:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)=[N:13][CH:14]=2)O1.C(OO)(C)=[O:38]>C1COCC1>[OH:38][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[C:18]([CH:33]=[CH:34][CH:35]=2)[CH:19]=[C:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:24][CH2:25]2)=[N:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 6585Peracetic AcidHCID 66875728Tert-butyl 4-(3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Produkt 1

HCID 66875736tert-Butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylateAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-(3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (3.45 g, 7 mmol) in THF (15 mL) was added AcOOH (4.6 mL, 60.67 mmol) at 0° C. The temperature was allowed to warm to RT and the reaction was stirred for 3 h. The reaction was quenched with Na2SO3 solution at 0° C. and the pH of the solution was adjusted to 7-7.5. Then the mixture was extracted with ethyl acetate and the organic layer was dried over Na2SO4 and concentrated to dryness. The residue was purified by silica gel column chromatography (1:3 acetone:hexane) to give the title compound (2.02 g, 75%). 1H NMR (500 MHz, DMSO-d6): δ 9.67 (s, 1H), 7.72 (s, 1H), 7.28 (m, 2H), 6.98 (d, J=7.2 Hz, 1H), 6.89 (d, J=8.5 Hz, 1H), 6.85 (d, J=7.5 Hz), 6.83 (s, 1H), 6.35 (s, 1H), 3.41 (m, 2H), 3.31 (m, 2H), 2.38 (m, 2H), 2.27 (m, 2H), 1.41 (s, 9H); m/z (383.1, M+ H+).

Aufarbeitung

  1. customThe reaction was quenched with Na2SO3 solution at 0° C.
  2. extractionThen the mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by silica gel column chromatography (1:3 acetone:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ffc9df7cb4d44879a82c4a930541c700
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

Notizen zur Reaktion

Wird geladen…