HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → (2S, 3S)-1-tert-Butoxycarbonyl-2-phenyl-3-(5-(2,2,2-trifluoro-1-(trifluoromethyl)ethyl)-2-methoxybenzyl)aminopiperidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | (2S,3S)-3-Amino-1-tert-butoxycarbonyl-2-phenylpiperidine | HCID 11311934 | — |
| Reactant | 5-(2,2,2-Trifluoro-1-(trifluoromethyl)ethyl)-2-methoxybenzaldehyde | HCID 18677614 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2S, 3S)-1-tert-Butoxycarbonyl-2-phenyl-3-(5-(2,2,2-trifluoro-1-(trifluoromethyl)ethyl)-2-methoxybenzyl)aminopiperidine | HCID 15549735 | 103.7% |
Reaction Steps
To a stirred and ice-cooled solution of Compound 12 (100 mg, 0.3 mmol) and Compound 9 (100 mg, 0.3 mmol) in dry CH2Cl2 (10 ml) was added NaBH(OAc)3 (210 mg, 1 mmol) in one portion. After the mixture was stirred at room temperature for 20 hours. The mixture was poured into NaHCO3 aq., and extracted with CH2Cl2. The combined extracts were dried (Na2SO4), and concentrated in vacuo to give Compound 13 as a yellow oil (170 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06329396B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-faa1df779fb44fd3b033ead414aea187 |
| Source note | uspto-grants-2001_12 |