Formaldehyde → HCID 52917807, Verbindung

HRID 551548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551548
Cl.[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][NH:4]1.[CH2:8]=O.[CH3:10][C:11]1[CH:12]=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][C:17]([C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)=[CH:16][CH:15]=2>CCO>[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:10][C:11]1[CH:12]=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][C:17]([C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)=[CH:16][CH:15]=2

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 11147704(2R)-(-)-2-Methylpyrrolidine hydrochlorideHCID 67104661HCID 67104661, Verbindung

Produkt 1

HCID 52917807HCID 52917807, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

(2R)-2-Methylpyrrolidine hydrochloride 5 (973 mg, 8.0 mmol) and 37% aqueous solution of formaldehyde (0.57 mL, 7.0 mmol) were combined in EtOH (20 mL) and heated in a sealed tube at 85° C. for 1 hour. The mixture was allowed to cool to room temperature, treated with the products from Example 61C (500 mg, 2.0 mmol), and heated at 85° C. overnight. The mixture was allowed to cool to room and concentrated to dryness under vacuum. The residue was partitioned between IPAc (50 mL) and 20% brine (40 mL). The organic layer was separated, dried with Na2SO4, filtered, and the filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with heptane:acetone:CH2Cl2:Et3N (60:40:3:1) to provide the title compounds. MS 343 (M+H)+; 1H NMR (400 MHz, CDCl3) δ 8.74 (s, 1H), 7.72 (s, 1H), 8.16 (m, 2H), 8.06 (m, 2H), 7.85 (m, 2H), 7.70 (m, 4H), 3.17 (m, 8H), 2.52 (m, 2H), 2.31 (m, 2H), 2.17 (m, 2H), 1.83 (m, 2H), 1.65 (m, 4H), 1.32 (m, 2H). 13C NMR (400 MHz, CDCl3) δ 156.63, 156.41, 146.45, 145.16, 143.73, 143.70, 141.75, 141.53, 140.81, 140.60, 139.89, 139.04, 132.38, 129.66, 129.36, 128.42, 127.68, 127.65, 127.55, 137.13, 126.86, 118.29, 111.48, 111.40, 59.87, 53.93, 52.89, 35.83, 32.90, 21.98, 19.25.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. temperatureheated at 85° C. overnight
  3. temperatureto cool to room
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue was partitioned between IPAc (50 mL) and 20% brine (40 mL)
  6. customThe organic layer was separated
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under vacuum
  10. customThe residue was purified by silica gel column chromatography
  11. washeluting with heptane:acetone:CH2Cl2:Et3N (60:40:3:1)

Quellen und Nachweise

ORD-Eintrag
ord-a6241cce53c14e9984c907a363c36a66
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947711B2

Notizen zur Reaktion

Wird geladen…