Tetrahydrofuran → HCID 71227791, compound

Reaction equation

[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

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 25517Ammonium Chloride

HCID 131736724HCID 131736724, compound

HCID 178418689HCID 178418689, compound

Product 1

HCID 71227791HCID 71227791, compoundYield 133%

Procedure

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.