Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86701829, compound
Reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[Li]N([Si](C)(C)C)[Si](C)(C)C.[CH3:16][N:17]1[C:21]2[C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH2:26][C:20]=2[C:19]([C:28]([O:30]CC)=O)=[N:18]1>C1COCC1>[CH3:5][O:4][N:3]([CH3:2])[C:28]([C:19]1[C:20]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22](=[O:27])[C:21]=2[N:17]([CH3:16])[N:18]=1)=[O:30]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of N,O-dimethylhydroxylamine hydrochloride (650 mg, 0.67 mmol) in 2 mL of anhydrous THF under argon, 1M solution of LiN(TMS)2 in THF (1.32 mL, 1.32 mmol) at 0° C. were added dropwise. The mixture was stirred at 0° C. for 0.5 h then ethyl 1-methyl-8-oxo-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxylate (50 mg, 0.22 mmol) in 5 mL of anhydrous THF at 0° C. were added dropwise. Ice bath was removed and the mixture was stirred at room temperature overnight. Water (20 mL) was added and the mixture was extracted with AcOEt (2×30 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent evaporated to dryness. The crude solid was used without further purification. 52 mg (quantitative yield).
Workup
- customIce bath was removed
- stirringthe mixture was stirred at room temperature overnight
- additionWater (20 mL) was added
- extractionthe mixture was extracted with AcOEt (2×30 mL)
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- customthe solvent evaporated to dryness
- customThe crude solid was used without further purification
Sources & evidence
- ORD record
- ord-2cd96011383745189383665d96d6f376
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916577B2
Reaction notes
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