Ethyl Acetate → (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid

HRID 379978

Reaktionsgleichung

Reaktionsgleichung von HRID 379978
C([Li])(C)(C)C.Br[C:7]1[CH:32]=[CH:31][C:10]([O:11][C@@H:12]([CH3:30])[C@H:13]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:9][CH:8]=1.C([O:36][B:37](OC(C)C)[O:38]C(C)C)(C)C.C(OCC)(=O)C>O1CCCC1>[Si:23]([O:22][C@H:13]([CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[C@H:12]([CH3:30])[O:11][C:10]1[CH:31]=[CH:32][C:7]([B:37]([OH:38])[OH:36])=[CH:8][CH:9]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 21531Triisopropyl borateHCID 57150561(3R,4S)-3-[4-(4-Bromo-phenoxy)-3-(tert-butyl-dimethyl-silanyloxy)-pentyl]-pyridineHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 54020751(1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Prepared according to the method described in Example 5b) from tert-butyllithium (3.95 ml, 1.7M in hexanes), (3R,4S)-3-[4-(4-bromophenoxy)-3-(tert-butyldimethyl-silanyloxy)pentyl]pyridine (2.52 g, Example 11b)) and tri-isopropylborate (1.68 ml) in tetrahydrofuran (20 ml) to afford the sub-title compound as a foam (1.22 g) after chromatography on silica eluting with ethyl acetate and then ethyl acetate:methanol (4:1).

Aufarbeitung

  1. customPrepared

Quellen und Nachweise

ORD-Eintrag
ord-b10f7ea6fca647a99796278aa83dd931
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300352B1

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