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Lithium hexamethyldisilazane → N,N-Bis(trimethylsilyl)-(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutylamine

HRID 1037733
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1037733
[CH3:1][Si:2]([N-:5][Si:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])[CH3:3].[Li+].Cl[C@@H:12]([B:17]1[O:21][C@@H:20]2[CH2:22][C@@H:23]3[CH2:26][C@H:25]([C@:19]2([CH3:29])[O:18]1)[C:24]3([CH3:28])[CH3:27])[CH2:13][CH:14]([CH3:16])[CH3:15]>O1CCCC1>[CH3:1][Si:2]([CH3:4])([CH3:3])[N:5]([C@H:12]([B:17]1[O:21][C@@H:20]2[CH2:22][C@@H:23]3[CH2:26][C@H:25]([C@:19]2([CH3:29])[O:18]1)[C:24]3([CH3:27])[CH3:28])[CH2:13][CH:14]([CH3:16])[CH3:15])[Si:6]([CH3:9])([CH3:8])[CH3:7]
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Komponenten

4

Edukt 2

HCID 2733832Lithium hexamethyldisilazaneHCID 21103224(3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole

Produkt 1

HCID 21103230N,N-Bis(trimethylsilyl)-(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (189 ml, 0.189 mol) was added, over 30 minutes, to a solution of crude 2-[(1S)-1-chloro-3-methylbutyl]-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole of Step 2 (59.0 g, 91% purity, 0.189 mol) in tetrahydrofuran (580 ml) while cooling at −78° C. The reaction mixture was allowed to slowly warm to room temperature overnight. The solvent was removed by rotary evaporation and the residue taken up with dry hexane (800 ml). The resulting suspension was stirred at room temperature for 2 hours, then the solid was removed by filtration on a celite cake, which was washed with dry hexane (3×100 ml). The filtrate was concentrated giving a satisfactorily pure product as a brown oil (79 g) in practically quantitative yield. The product was used for the subsequent step without further purification.

Aufarbeitung

  1. temperatureto slowly warm to room temperature overnight
  2. customThe solvent was removed by rotary evaporation
  3. customthe solid was removed by filtration on a celite cake, which
  4. washwas washed with dry hexane (3×100 ml)
  5. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-72411ae1ac9847f1bea0d42d61a894ed
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546608B2

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