Hydrochloric Acid → (2R)-1-methoxy-4-methyl-pentan-2-amine
Reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([N:9]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:5][CH:6]([CH3:8])[CH3:7].O.NN.Cl>CO>[CH3:1][O:2][CH2:3][C@H:4]([NH2:9])[CH2:5][CH:6]([CH3:8])[CH3:7]Participants
5
Conditions
- Temperature
- 45 °C
Procedure
To a solution of (R)-2-(1-methoxy-4-methylpentan-2-yl)isoindoline-1,3-dione (example 9b) (3.87 g, 14.84 mmol) in methanol (30 mL), was added hydrazine hydrate (0.866 ml, 17.81 mmol) and the reaction mixture was warmed up to 45° C. for about 3 hours. The mixture was acidified with 2N HCl and stirred at 45° C. for 30 min. The solution was cooled to room temperature, filtered and evaporated. The residue was taken up with 2N NaOH and extracted with ether, dried over MgSO4, filtered and evaporated to give 1.51 g of (R)-1-methoxy-4-methylpentan-2-amine. Yield 77%. 1H NMR (500 MHz, CDCl3): 0.91 (m, 6H); 1.17 (m, 2H); 1.58 (s, 2H); 1.71 (m, 1H); 3.02 (m, 1H); 3.10 (m, 1H); 3.32 (m, 1H); 3.35 (s, 3H).
Workup
- temperatureThe solution was cooled to room temperature
- filtrationfiltered
- customevaporated
- extractionextracted with ether
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-5ed9ca76d11f4f9fbf26c16186c8b5be
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895050B2
Reaction notes
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