Ammonium Chloride → tert-Butyl (S)-5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate
Reaction equation
[C:1]([O:5][C:6]([C@H:8]1[N:12]=[C:11](SC)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+:15].[Cl-]>CO>[C:1]([O:5][C:6]([C@H:8]1[N:12]=[C:11]([NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
4
Procedure
To a solution of (S)-2-methylsulfanyl-3,4-dihydro-5H-pyrrole-5-carboxylic acid t-butyl ester (0.42 g, 1.95 mmol) in 4.0 mL anhydrous MeOH was added anh NH4Cl (0.11 g, 2.05 mmol). The reaction mixture was heated to reflux for 2 h, concentrated in vacuo, and the residue was taken up in CH2C2. The white solids were filtered, and the filtrate was concentrated to provide (S)-2-amino-3,4-dihydro-5H-pyrrole-5carboxylic acid t-butyl ester.HCl (0.41 g, 94%) as a light yellow solid 1H NMR (CDCl3) δ 1.49 (s, 9H), 2.24 (m, 1H), 2.52 (m, 1H), 3.06-3.08 (m, 2H), 4.44 (m, 1H), 9.81-9.8 (m, 2H). MS calcd for C9H16N2O2 +H 185, found 185.