Formaldehyde → 4-(1-Triisopropylsilanyl-1H-pyrrol-3-ylmethyl)-morpholine

HRID 1093972

Reaktionsgleichung

Reaktionsgleichung von HRID 1093972
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:7]([Si:10]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)([CH3:9])[CH3:8].[CH2:22]=O.[OH-].[Na+]>C(O)(=O)C.O>[CH:19]([Si:10]([CH:7]([CH3:9])[CH3:8])([CH:16]([CH3:18])[CH3:17])[N:11]1[CH:15]=[CH:14][C:13]([CH2:22][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:12]1)([CH3:21])[CH3:20]

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 145136N-Triisopropylsilylpyrrole

Produkt 1

HCID 666367604-(1-Triisopropylsilanyl-1H-pyrrol-3-ylmethyl)-morpholine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of morpholine (98.5 mmoles) in acetic acid (100 ml) at 0° C. there are added 1-triisopropylsilanyl-1H-pyrrole (89.5 mmoles) and formaldehyde (89.5 mmoles) 37% in water. The reaction mixture is stirred overnight at ambient temperature. The solution is brought to alkaline pH (10-12) using 20% aqueous NaOH solution and is then extracted with DCM. The organic phase is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue obtained is purified by flash chromatography on silica gel (SiO2; gradient DCM/AcOEt) to yield the title product, which is used directly in the next Step.

Aufarbeitung

  1. extractionis then extracted with DCM
  2. washThe organic phase is washed with water and with saturated aqueous NaCl solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue obtained
  7. customis purified by flash chromatography on silica gel (SiO2; gradient DCM/AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-54b2d334f85d4838b10f400874ce569a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133889B2

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