HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 68502068, 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 86622958 | HCID 86622958 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 68502068 | HCID 68502068 | 50.4% |
Reaction Steps
A mixture of [2-(4-chloro-3-formyl-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester (325 mg, 1.09 mmol), Et3N (0.228 mL, 1.64 mmol) and cyclopropylamine (0.115 mL, 1.64 mmol) in MeOH (3.66 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (103 mg, 2.73 mmol) was added. The mixture was stirred for 1 h at rt, and aq. sat. NaHCO3 was added. The mixture was extracted with EtOAc several times. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC yielded the title compound (186 mg, 50%). LC-MS: tR=0.79 min; ES+: 339.39.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07799805B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-fd722ea5e14c4ebd9f207f179c16b93e |
| Source note | uspto-grants-2010_09 |