Methylhydrazine → (3-Aminopropoxy)(tert-butyl)dimethylsilane
Reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CNN>C(O)C>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][NH2:12])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of N-(3-hydroxypropyl)phthalimide (5.25 g, 24.36 mmol) in DMF (20 mL) was added imidazole (16.6 g, 240 mmol) and tert-butyldimethylsilyl chloride (19 g, 120 mmol). The reaction was stirred at room temperature for 18 hours before the volatiles were removed in vacuo and a portion of the crude product was subjected to column chromatography (SiO2, 1:1 DCM/hexanes) to give 2-[3-(tert-butyldimethylsilanyloxy)propyl]isoindole-1,3-dione as a clear oil (5 g). 2-[3-(tert-Butyldimethylsilanyloxy)propyl]isoindole-1,3-dione (5 g, 26.4 mmol) was dissolved in ethanol (50 ml) and methyl hydrazine (2.94 ml, 55.4 mmol) added. The reaction was heated to 75° C. for 8 hours before concentration in vacuo. The crude residue was triturated with a mixture of diethyl ether (150 mL) and hexanes (50 mL) and the resultant solid removed by filtration. The solvents were removed in vacuo to give the title compound as a pale yellow oil (1.8 g, 61%). δH (DMSO-d6) 4.58 (2H, br s), 3.63-3.58 (2H, m), 2.67-2.62 (2H, m), 1.60-1.55 (2H, m), 0.83 (9H, d, J 1.1 Hz), 0.00 (6H, d, J 1.2 Hz). LCMS (ES+) RT 1.77 minutes, 190 (M+H)+.
Workup
- customThe crude residue was triturated with a mixture of diethyl ether (150 mL) and hexanes (50 mL)
- customthe resultant solid removed by filtration
- customThe solvents were removed in vacuo
Sources & evidence
- ORD record
- ord-2985643a26aa4b169b9728a7872c3799
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283359B2
Reaction notes
Loading…