Benzyl Bromide → HCID 67382789, compound

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[NH2:7][C@H:8]1[CH2:12][CH2:11][C@@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9]1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH2:17]([NH:7][C@H:8]1[CH2:12][CH2:11][C@@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Procedure

Potassium carbonate (462 mg, 3.30 mmol) was added to a solution of (1R,3S)-methyl 3-aminocyclopentanecarboxylate (400 mg, 2.22 mmol) in MeOH (10 ml) and stirred for 1 h. Benzyl bromide (0.2 ml, 1.8 mmol) was added to the reaction mixture and stirred for 15 h at 60-65° C. The reaction mixture was concentrated and the resulting residue was partitioned between water and CHCl3. The organic layer was separated and washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford the crude product. Purification by column chromatography over neutral alumina using 2% MeOH in CHCl3 as eluent afforded 180 mg of (1R,3S)-methyl 3-(benzylamino)cyclopentanecarboxylate with a purity of 75% which was proceeded for the next step.