Morpholine → tert-Butyl 4-(3-morpholinopyrrolidin-1-yl)benzoate

HRID 1907742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907742
O=[C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:19]=[CH:18][C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.C([Sn](Cl)(Cl)CCCC)CCC.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C1([SiH3])C=CC=CC=1>COCCOC.CO.O>[O:34]1[CH2:35][CH2:36][N:31]([CH:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:19]=[CH:18][C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][CH:8]=3)[CH2:3]2)[CH2:32][CH2:33]1

Komponenten

8

Edukt 4

HCID 8083MorpholineHCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 10015517Tert-butyl 4-(3-oxopyrrolidin-1-yl)benzoate

Produkt 1

HCID 59737295tert-Butyl 4-(3-morpholinopyrrolidin-1-yl)benzoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of ketone 267 (0.40 g, 1.53 mmol), dibutyltin dichloride (0.35 g) and morpholine (0.27 mL) in ethyleneglycol dimethylether (3.5 mL) was stirred at room temperature for 6 h, then cooled to 0° C. for the addition of neat phenyl silane (0.60 mL, 4.72 mmol). The reaction mixture was stirred at room temperature for 18 h then diluted with MeOH (3 mL) and H2O (0.5 mL), stirred for additional 4 h and concentrated. The residue was purified by flash chromatography (eluent: 5% MeOH in DCM) to provide title compound 268 (0.56 g, >100% yield, crude, used without additional purification).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. stirringstirred for additional 4 h
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (eluent: 5% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-e05b11474ea44ec980d6b7910a7e217b
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598168B2

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