Methylhydrazine → tert-Butyl (S)-3-(aminooxy)pyrrolidine-1-carboxylate
Reaction equation
CNN.[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([O:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(Cl)Cl>[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([O:16][NH2:17])[CH2:12]1)=[O:10])([CH3:7])([CH3:5])[CH3:6]Participants
4
Procedure
Methyl hydrazine (0.23 mL, 4.40 mmol) was added dropwise over 5 minutes to a solution of (S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.43 g, 4.3 mmol) in DCM (12 mL). The mixture was stirred at ambient temperature for 1 hour then evaporated. The resultant residue was suspended in diethyl ether (10 mL) and the solid was filtered. The filtrate was concentrated to provide the title compound as a colourless oil (0.86 g, 99%). 1H NMR (CDCl3, 400 MHz) 4.24-4.26 (m, 1H), 3.60-3.66 (m, 1H), 3.44-3.54 (m, 1H), 3.30-3.42 (m, 2H), 2.03-2.12 (m, 1H), 1.84-1.96 (m, 1H), 1.46 (s, 9H).