Chlorotrimethylsilane → (R)-N,N-dimethyl-2-(2-neopentyl-5-(pyrrolidin-3-ylsulfonyl)-1H-benzo[d]imidazol-1-yl)ethanamine

HRID 241674

Reaktionsgleichung

Reaktionsgleichung von HRID 241674
[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([C@@H:17]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)(=[O:16])=[O:15])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31].Cl[Si](C)(C)C>CO>[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([C@@H:17]3[CH2:21][CH2:20][NH:19][CH2:18]3)(=[O:15])=[O:16])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:29][C:30]([CH3:32])([CH3:31])[CH3:33]

Komponenten

4

Edukt 2

HCID 6397ChlorotrimethylsilaneHCID 58513604(R)-tert-butyl 3-(1-(2-(dimethylamino)ethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 58513585(R)-N,N-dimethyl-2-(2-neopentyl-5-(pyrrolidin-3-ylsulfonyl)-1H-benzo[d]imidazol-1-yl)ethanamineAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of (R)-tert-butyl 3-(1-(2-(dimethylamino)ethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)pyrrolidine-1-carboxylate (STEP B, 612 mg, 1.24 mmol) in methanol (5 mL) was added chlorotrimethylsilane (749 microL, 6.21 mmol). The mixture was stirred at 50° C. for 3 h. The mixture was concentrated in vacuo. To the residue was added 2 mol/L sodium hydroxide aqueous solution to pH>7 and the mixture was extracted with ethyl acetate (150 mL). The organic layer was washed with brine and dried over sodium sulfate. The resulting solution was concentrated to give the title compound (453 mg, 93%) as an oil.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. additionTo the residue was added 2 mol/L sodium hydroxide aqueous solution to pH>7
  3. extractionthe mixture was extracted with ethyl acetate (150 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe resulting solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d519c11abe5146429d739ddd8bed1bf6
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653063B2

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