Triethylamine → tert-Butyl [3-(cyclopropylamino)propyl]methylcarbamate

The compound (300 mg, 1.59 mmol) obtained in Example 25b was dissolved in ethyl acetate (16 mL), triethylamine (0.323 mL, 2.39 mmol) and methanesulfonyl chloride (0.147 mL, 1.90 mmol) were added under ice cooling, and the mixture was stirred at the same temperature for 10 minutes. Insoluble matter was removed by filtration through celite, the solvent was evaporated under reduced pressure, the resulting residue was added dropwise to a solution of cyclopropylamine (1.82 g, 31.8 mmol) in methanol (3 mL) under ice cooling, and the mixture was stirred at 60° C. for 72 hours. The solvent was evaporated under reduced pressure, 1 N sodium hydroxide was added to the resulting residue, and the mixture was extracted with ethyl acetate (×3). The organic layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1→10:1, v/v) to give the title compound (215 mg; yield, 59%) as a yellow oily substance.

1. customInsoluble matter was removed by filtration through celite
2. customthe solvent was evaporated under reduced pressure
3. stirringthe mixture was stirred at 60° C. for 72 hours
4. customThe solvent was evaporated under reduced pressure, 1 N sodium hydroxide
5. additionwas added to the resulting residue
6. extractionthe mixture was extracted with ethyl acetate (×3)
7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
8. customthe solvent was evaporated under reduced pressure
9. customthe resulting residue was purified by silica gel column chromatography (methylene chloride

ORD record

ord-16c981ecb2334acfa575e1c93fc88f71

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476253B2