Diisopropylethylamine → Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylate

HRID 16589

Reaktionsgleichung

Reaktionsgleichung von HRID 16589
I[CH2:2][C:3]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:12]([O:16][C:17](=[O:26])[NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C>CN1CCCC1=O.C([O-])(O)=O.[Na+]>[C:12]([O:16][C:17]([NH:18][CH2:19][CH:20]1[CH2:21][CH2:22][N:23]([CH2:2][C:3]2([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:24][CH2:25]1)=[O:26])([CH3:15])([CH3:13])[CH3:14]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 67231596Methyl 1-(iodomethyl)cyclopentanecarboxylate

Produkt 1

HCID 67232469Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylateAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 13387N-methyl-2-pyrrolidoneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of Methyl 1-(iodomethyl)cyclopentanecarboxylate(5.52 g, 0.0206 mol, Step 1), tert-butyl(piperidin-4-ylmethyl)carbamate (8.83 g, 0.0412 mol) and iPr2NEt (10.76 mL, 0.0618 mol) in N-methylpyrrolidone (70 mL) was stirred at 120° C. for 24 h. After cooling, the reaction mixture was diluted with sat. NaHCO3 aq. (200 mL), extracted with AcOEt (200 mL) for three times, and the combined organic layer was washed with water (200 mL) and brine (200 mL). The organic layer was dried over Na2SO4, filtered and concentrated. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1) to give 4.91 g (67%) of title compound as a yellow syrup.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with AcOEt (200 mL) for three times
  3. washthe combined organic layer was washed with water (200 mL) and brine (200 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customRemoval of the solvent
  8. customgave a residue, which
  9. customwas chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-7979378220074b7c996aa06eafdcf99f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737163B2

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