2-(4-Bromo-2-chloro-phenyl)-1,1,1,3,3,3-hexamethyl-disilazane → 2-Butyl-2-{[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-phenyl]-hydroxy-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 661542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661542
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([Si:13]([CH3:16])([CH3:15])[CH3:14])[Si:9]([CH3:12])([CH3:11])[CH3:10])=[C:4]([Cl:17])[CH:3]=1.C([Li])(C)(C)C.[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C:31]1([CH2:37][CH2:38][CH2:39][CH3:40])[CH:35]=[O:36])=[O:29])([CH3:26])([CH3:25])[CH3:24]>CCOCC>[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C:31]1([CH2:37][CH2:38][CH2:39][CH3:40])[CH:35]([C:2]1[CH:7]=[CH:6][C:5]([N:8]([Si:13]([CH3:16])([CH3:15])[CH3:14])[Si:9]([CH3:12])([CH3:11])[CH3:10])=[C:4]([Cl:17])[CH:3]=1)[OH:36])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Komponenten

5

Edukt 3

HCID 547539992-(4-Bromo-2-chloro-phenyl)-1,1,1,3,3,3-hexamethyl-disilazaneHCID 866208582-Butyl-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 666875552-Butyl-2-{[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-phenyl]-hydroxy-methyl}-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 2-(4-bromo-2-chloro-phenyl)-1,1,1,3,3,3-hexamethyl-disilazane (0.484 g, 1.38 mmol) in ether (14 mL) at −78° C. and under nitrogen was added tert-butyllithium (2.03 mL, 1.43 M solution in pentanes, 2.91 mmol) dropwise. After 90 minutes, a solution of 2-butyl-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.353 g, 1.38 mmol) in ether (3 mL) was added to the reaction mixture dropwise. After one hour, the reaction mixture was warmed to ambient temperature and stirred at ambient temperature for 30 minutes. The reaction mixture was quenched by the addition of saturated aqueous NH4Cl (10 mL) and extracted with EtOAc. The combined extracts were washed with brine, then dried (MgSO4), filtered, and concentrated in vacuo to an oil (0.75 g). Purification by chromatography (silica, 5-20% EtOAc in hexanes) gave 2-butyl-2-{[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-phenyl]-hydroxy-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (0.357 g, 0.678 mmol, 49%) as a colourless oil.

Aufarbeitung

  1. waitAfter one hour
  2. customThe reaction mixture was quenched by the addition of saturated aqueous NH4Cl (10 mL)
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to an oil (0.75 g)
  8. customPurification by chromatography (silica, 5-20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e9950238aab34bcabd1297b0872a5111
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084623B2

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