HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → (2S,3S)-1-tert-Butoxycarbonyl-3-(5-(1-cyanoethyl)-2-methoxybenzyl)amino-2-phenylpiperidine
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-(1-Cyanoethyl)-2-methoxybenzaldehyde | HCID 19066487 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2S,3S)-1-tert-Butoxycarbonyl-3-(5-(1-cyanoethyl)-2-methoxybenzyl)amino-2-phenylpiperidine | HCID 57028229 | 103.8% |
Reaction Steps
To a stirred and ice-cooled solution of Compound 17 (160 mg, 0.60 mmol) and Compound 14 (120 mg, 0.60 mmol) in dry CH2Cl2 (5 ml) was added NaBH(OAc)3 (430 mg, 2.0 mmol) in one portion. 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 18 as a yellow oil (280 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05789423 |
| Source dataset | uspto-grants-1998_08 |
| ORD ID | ord-6d9f25a64db247fdb285099b400e9bed |
| Source note | uspto-grants-1998_08 |