Tetrahydrofuran → HCID 71227791, 화합물

반응식

[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

참가 물질

반응물 4

HCID 8028Tetrahydrofuran

HCID 25517Ammonium Chloride

HCID 131736724HCID 131736724, 화합물

HCID 178418689HCID 178418689, 화합물

생성물 1

HCID 71227791HCID 71227791, 화합물수율 133%

실험 절차

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.