HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (S)-4-(4-Bromo-2,5-difluorobenzyl)-3-methylmorpholine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 4-Bromo-2,5-difluorobenzaldehyde | HCID 22489081 | — |
| Reactant | (3S)-3-methylmorpholine hydrochloride | HCID 53486469 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Product | (S)-4-(4-Bromo-2,5-difluorobenzyl)-3-methylmorpholine | HCID 59543858 | 94.1% |
Reaction Steps
4-Bromo-2,5-difluorobenzaldehyde (331 mg, 1.5 mmol), (S)-3-methylmorpholine hydrochloride (206 mg, 1.50 mmol) and sodium triacetoxyborohydride (461 mg, 2.18 mmol) were mixed in dichloroethane (5 mL). Triethylamine (0.230 mL, 1.65 mmol) was added and the resulting mixture was stirred at RT under argon atmosphere for 24 h. NaHCO3 (25 mL) was added and the mixture was extracted with dichloromethane (3×25 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated to give (S)-4-(4-bromo-2,5-difluorobenzyl)-3-methylmorpholine (432 mg, 94%) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178529B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-7db1490fb085401faa18fa6064368682 |
| Source note | uspto-grants-2012_05 |