HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Phosphate, Tribasic → {1-[3-(3-Dimethylamino-pyrrolidin-1-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | (3R)-(+)-3-(Dimethylamino)pyrrolidine | HCID 2758521 | — |
| Reactant | (S)-N-Boc-1-(3-bromophenyl)ethylamine | HCID 56971804 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | {1-[3-(3-Dimethylamino-pyrrolidin-1-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester | HCID 69588726 | 27% |
Reaction Steps
A mixture of (S )[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (6 g), (3R)-3-(dimethylamino)-pyrrolidine (4.56 g), Pd2(dba)3 (1.83 g), di-t-butyl-biphenylphosphine (600 mg), K3PO4 (8.48 g) in DME (40 mL) was stirred at reflux for 16 h. The reaction mixture was cooled down to room temperature, diluted with methylene chloride, and filtered. The filtrated was evaporated in vacuo, and the crude product was purified by Flash Chromatography using Biotage eluting with 20% MeOH in ethyl acetate to give the title compound (1.8 g) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07144881B2 |
| Source dataset | uspto-grants-2006_12 |
| ORD ID | ord-25c8f9ac53e244bba0ba6badd5929881 |
| Source note | uspto-grants-2006_12 |