Methylhydrazine → (3-Aminopropoxy)(tert-butyl)dimethylsilane
Reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][CH2:8][CH2:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].CNN>C(O)C>[Si:5]([O:6][CH2:7][CH2:8][CH2:9][NH2:10])([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:22])[CH3:21]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-butyldimethyl-silanyloxy)propyl]isoindole-1,3-dione as a clear oil (5 g). 2-[3-(tert-Butyldimethyl-silanyloxy)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-c99e4964deac4e058fa0eba9d4af0bb8
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394822B2
Reaction notes
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