Potassium Carbonate → HCID 23570952, compound

To a solution of (3-methoxy-phenyl)-acetic acid methyl ester (19.6 mmol) in CCl4 was added N-bromosuccinimide (19.6 mmol) and the reaction mixture was irradiated for 2 hours. The reaction mixture was then concentrated in vacuo to afford the intermediate bromo-(3-methoxy-phenyl)-acetic acid methyl ester. To a solution of bromo-(3-methoxy-phenyl)-acetic acid methyl ester in THF (30 mL) under an atmosphere of nitrogen was added a solution of (2-amino-ethyl)-carbamic acid tert-butyl ester (20.6 mmol) in THF (20 mL) followed by K2CO3 (39.2 mmol, 2 equivalents). The reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was partitioned between water (50 mL) and EtOAc (2×50 mL), the combined organics were dried (sodium sulfate) and concentrated in vacuo to afford an oil. The oil was purified by silica gel column chromatography using as eluent EtOAc:petrol (1:1) to give the title compound as an oil in 53% yield.

1. customThe reaction mixture was partitioned between water (50 mL) and EtOAc (2×50 mL)
2. dry with materialthe combined organics were dried (sodium sulfate)
3. concentrationconcentrated in vacuo
4. customto afford an oil
5. customThe oil was purified by silica gel column chromatography

ORD record

ord-ea60a30629e44818b8020be8cd25700e

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07041687B2