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Triisopropyl borate → tert-Butyl [5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate

HRID 1851779
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1851779
[Li]CCCC.Br[C:7]1[CH:8]=[CH:9][C:10]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:11][CH:12]=1.C(O[B:26](OC(C)C)OC(C)C)(C)C.[OH:35][CH2:36][C:37]([CH3:41])([CH2:39][OH:40])[CH3:38]>C1COCC1>[CH3:38][C:37]1([CH3:41])[CH2:39][O:40][B:26]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:11][CH:12]=2)[O:35][CH2:36]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 21531Triisopropyl borateHCID 31344Neopentyl glycolHCID 45789881tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamateHCID 178418339Butyllithium

Produkt 1

HCID 86626541tert-Butyl [5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamateAusbeute 11,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-BuLi (27 mL, 2.5 M) was slowly added to a stirred solution of tert-butyl (5-bromopyridin-2-yl)methylcarbamate (17.7 g, 61.6 mmol) in THF (280 mL) at −78° C. under an argon atmosphere. After 5 min at −78° C., triisopropylborate (28.5 mL, 123 mmol) was added and the mixture was stirred at −78° C. for 1 h. Neopentyl glycol (6.4 g, 61.4 mmol) was added and the reaction mixture was allowed to reach rt and was stirred for 2.5 d. The reaction was quenched with water (300 mL). The phases were separated and the aqueous phase was extracted with DCM. The organic layer was concentrated and the residue was purified by two successive flash chromatographies (Heptane/EtOAc 9:1→1:4 and DCM/MeOH 24:1 respectively) to give the product (2.23 g) as a white solid. 1H NMR 8.57 (dd, 1 H) 7.94 (dd, 1 H) 7.65 (dd, 1 H) 3.76 (s, 4 H) 3.30 (s, 3 H) 1.47 (s, 9 H) 0.96 (s, 6 H).

Aufarbeitung

  1. customto reach rt
  2. stirringwas stirred for 2.5 d
  3. customThe reaction was quenched with water (300 mL)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with DCM
  6. concentrationThe organic layer was concentrated
  7. customthe residue was purified by two successive flash chromatographies (Heptane/EtOAc 9:1→1:4 and DCM/MeOH 24:1 respectively)

Quellen und Nachweise

ORD-Eintrag
ord-37334a508a4f4ac491e95aa5e3251566
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08957215B2

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