HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 68504060, 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 86622956 | HCID 86622956 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 68504060 | HCID 68504060 | 48% |
Reaction Steps
A mixture of (4-chloro-3-formyl-benzyl)-cyclopropylmethyl-carbamic acid tert-butyl ester (1.00 g, 3.09 mmol), Et3N (0.646 mL, 4.64 mmol) and cyclopropylamine (0.325 mL, 4.64 mmol) in MeOH (10.5 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (292 mg, 7.71 mmol) was added. The mixture was stirred for 1 h, and aq. sat. NaHCO3 was added. The mixture was extracted with EtOAc (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (MeOH/CH2Cl2 1:49) yielded the title compound (535 mg, 48%). LC-MS: tR=0.81 min; ES+: 406.20.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07799805B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-ada5ea9a80084da8ba4192c01ee5c690 |
| Source note | uspto-grants-2010_09 |