HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 68508212, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 86622961 | HCID 86622961 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 68508212 | HCID 68508212 | 44.1% |
Reaction Steps
A mixture of [2-(4-chloro-3-formyl-phenyl)-ethyl]-ethyl-carbamic acid tert-butyl ester (80.1 mg, 0.257 mmol), Et3N (0.054 mL, 0.386 mmol) and cyclopropylamine (0.027 mL, 0.386 mmol) in MeOH (0.86 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (24.2 mg, 0.642 mmol) was added in portions. The mixture was stirred for 1 h, and aq. sat. NaHCO3 was added. The mixture was extracted with EtOAc several times, and the combined org. extracts were washed with brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (CH2Cl2/MeOH 95:5) yielded the title compound (40 mg, 44%). LC-MS: tR=0.81 min; ES+: 353.22.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07799805B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-617e27462b134b47bf687333d20ce9f5 |
| Source note | uspto-grants-2010_09 |