Methanol → HCID 57516630, compound

Temperature

50 °C

3-(3-Bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane-2,4-dione (4.25 g, 16.0 mmol) was suspended in 80 mL of THF. Borane dimethyl sulfide complex (14.2 mL of a 10.1 M solution) was added and the reaction was heated at 50° C. for 1 h. The reaction was cooled in an ice bath. Methanol (65 mL) was slowly added, followed by 150 mL of water. This mixture was extracted with EtOAc (2×) and the combined organics were dried over MgSO4 and concentrated. The residue was taken up in dichloromethane and the resulting suspension was filtered. The filtrate was concentrated and the residue was purified by SiO2 chromatography using a gradient of 0% to 20% ethyl acetate/heptane to afford 3.63 g (95%) of 3-(3-bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane as a white solid.

1. temperatureThe reaction was cooled in an ice bath
2. extractionThis mixture was extracted with EtOAc (2×)
3. dry with materialthe combined organics were dried over MgSO4
4. concentrationconcentrated
5. filtrationthe resulting suspension was filtered
6. concentrationThe filtrate was concentrated
7. customthe residue was purified by SiO2 chromatography

ORD record

ord-1c054b7a23c6458387e67a666133ac9b

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518945B2