Acetic Acid → 3-(4-Bromophenyl)-1-methylpyrrolidine

HRID 251800

Reaktionsgleichung

Reaktionsgleichung von HRID 251800
C=O.[C:3](O)(=O)C.[H-].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)=[CH:24][CH:23]=1>C(Cl)(Cl)Cl.C(O)C.C(OCC)(=O)C>[Br:21][C:22]1[CH:23]=[CH:24][C:25]([CH:28]2[CH2:32][CH2:31][N:30]([CH3:3])[CH2:29]2)=[CH:26][CH:27]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 534077073-(4-Bromophenyl)pyrrolidineHCID 131728610Triacetoxy borohydride hydride

Produkt 1

HCID 594284273-(4-Bromophenyl)-1-methylpyrrolidineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 21889567Chloroform ethanolLösungsmittel

Versuchsvorschrift

Formalin (0.0452 ml, 0.557 mmol), 0.0319 ml (0.557 mmol) of acetic acid, and 118 mg (0.557 mmol) of triacetoxy borohydride hydride were added to a solution of 42 mg (0.186 mmol) of 3-(4-bromophenyl)pyrrolidine, synthesized in the same manner as in Reference Example 1, in chloroform-ethanol 3:1 (2 ml), and the mixture was stirred at room temperature for 40 min. The reaction solution was diluted with ethyl acetate, and the diluted solution was washed with a 10% aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate, was filtered, and was then concentrated under the reduced pressure to give 43 mg (yield 97%) of the title compound.

Aufarbeitung

  1. washthe diluted solution was washed with a 10% aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationwas filtered
  4. concentrationwas then concentrated under the reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1019a3cfc2f14e03a0d9679cf0cdffc5
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07867980B2

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