tert-Butyldimethylsilyl chloride → (1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropylamine

HRID 549109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 549109
Cl.[NH2:2][C@@H:3]([C:6]([CH3:9])([OH:8])[CH3:7])[CH2:4][OH:5].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[NH4+:2].[OH-:5].[Si:10]([O:8][C:6]([CH3:9])([CH3:7])[C@H:3]([NH2:2])[CH2:4][O:5][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Komponenten

6

Edukt 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 18341280(2R)-2-amino-3-methylbutane-1,3-diol hydrochloride

Produkt 2

HCID 14923Ammonium HydroxideAusbeute 0,1 %HCID 86624119(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropylamineAusbeute 121 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

(2R)-2-amino-3-methylbutane-1,3-diol hydrochloride (4.32 g, 27.8 mmol) was dissolved in 10 mL of pyridine and the solution was stirred under N2. tert-Butyldimethylsilyl chloride (16.8 g, 111 mmol) and DMAP (339 mg, 2.8 mmol) were then added and the reaction mixture was heated to 65° C. After 3 days, the reaction was cooled and treated with in 3.5% NaH2PO4 solution. The solution was extracted with 200 mL CH2Cl2 and then with an additional 50 mL of CH2Cl2. The combined organic layers were washed with H2O and brine. The organic layer was then dried over Na2SO4, filtered and concentrate under reduced pressure. Chromatography (SiO2, 3% MeOH/CHCl3 with 0.1% NH4OH) gave (1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropylamine (5.85 g) as a light amber oil.

Aufarbeitung

  1. temperaturethe reaction was cooled
  2. extractionThe solution was extracted with 200 mL CH2Cl2
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0891655ba50547f684e7c6f1dd269592
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943609B2

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