Tetrahydrofuran → HCID 71227791, Verbindung

Reaktionsgleichung

[CH2:1]([N:8]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@H:9]1[CH2:13][CH2:12][C@H:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][Mg+].[Br-].[NH4+].[Cl-].[CH2:36]1[CH2:40][O:39]CC1>>[CH2:24]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]1[CH2:13][CH2:12][C@H:11]([C:40]([OH:39])([CH3:36])[CH3:31])[CH2:10]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

Edukt 4

HCID 8028Tetrahydrofuran

HCID 25517Ammonium Chloride

HCID 131736724HCID 131736724, Verbindung

HCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 71227791HCID 71227791, VerbindungAusbeute 133 %

Versuchsvorschrift

To a 0° C. solution of trans-benzyl 3-(dibenzylamino)cyclopentanecarboxylate (2.8 g, 7 mmol) in THF (250 mL) was added dropwise MeMgBr (23 mL, 70 mmol). After the addition, the reaction mixture was stirred at room temperature overnight. TLC (PE) showed the reaction was complete. The mixture was cooled and poured into sat. NH4Cl (300 mL) and extracted with EtOAc (100 mL*3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to give crude 2-(trans-3-(dibenzylamino)cyclopentyl)propan-2-ol (3 g, 133%) as a yellow liquid.