Isopropylamine → tert-Butyl [3-(isopropylamino)propyl]methylcarbamate

tert-Butyl (3-hydroxypropyl)methylcarbamate (430 mg, 2.27 mmol) was dissolved in dichloromethane (5 mL), triethylamine (0.633 mL, 4.55 mmol) and methanesulfonyl chloride (0.262 mL, 3.41 mmol) were added under ice cooling, and the mixture was stirred at the same temperature for 10 minutes. Isopropylamine (1.3 g, 23 mmol) was further added, and then the mixture was stirred overnight at room temperature. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, the mixture was extracted with methylene chloride (×3), and the resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (elution solvents, n-hexane:ethyl acetate=9:1→1:1, v/v) to give the title compound (362 mg; yield, 73%).

1. stirringthe mixture was stirred overnight at room temperature
2. extractionthe mixture was extracted with methylene chloride (×3)
3. dry with materialthe resulting organic layer was dried with anhydrous sodium sulfate
4. customThe solvent was evaporated under reduced pressure
5. customthe resulting residue was purified by NH silica gel column chromatography (
6. washelution solvents, n-hexane

ORD record

ord-f2ab5709a0754520aa89bad32aedcb69

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476253B2