Methyl iodide → HCID 86711837, compound

tert-Butyl (1-hydroxycyclopropyl)methylcarbamate (150 mg) was dissolved in dry DMF (2 mL) and Cs2CO3 (313 mg, 0.961 mmol) was added, followed by MeI (0.053 mL, 0.841 mmol). The light yellow suspension was stirred in a sealed vessel at room temperature overnight. More MeI (0.050 mL, 0.801 mmol) was added and stirring was continued for 2 d. The reaction mixture was partitioned between aqueous saturated NaHCO3 (25 mL) and EtOAc (25 mL). The aqueous layer was extracted with EtOAc (2×10 mL) and the combined organic layers were washed with saturated aqueous NaHCO3 (2×25 mL). The organic layer was washed with brine (2×25 mL) and dried on Na2SO4 before concentration in vacuo to give a yellow oil. The product was filtered over a plug of silica (eluent heptane/iPr2O 1:1) to give the title compound (90 mg, 16% from 1-(aminomethyl)cyclopropanol) as a colorless oil.

1. stirringstirring
2. waitwas continued for 2 d
3. customThe reaction mixture was partitioned between aqueous saturated NaHCO3 (25 mL) and EtOAc (25 mL)
4. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
5. washthe combined organic layers were washed with saturated aqueous NaHCO3 (2×25 mL)
6. washThe organic layer was washed with brine (2×25 mL)
7. customdried on Na2SO4 before concentration in vacuo
8. customto give a yellow oil
9. filtrationThe product was filtered over a plug of silica (eluent heptane/iPr2O 1:1)

ORD record

ord-4f0aecdc48ec4d1a95626a127a78e0a4

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302988B2