HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → HCID 68616941, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Ethylamine | HCID 6341 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | (3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 59512275 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | HCID 68616941 | HCID 68616941 | — |
Reaction Steps
The title compound is prepared from (3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.75 g, 1.52 mmol), 2N solution of ethylamine in MeOH (3.805 mL, 7.61 mmol) and NaBH4 (0.115 g, 3.04 mmol) and purification by flash chromatography on silica gel (CH2Cl2/MeOH 96:4, then CH2Cl2/MeOH (10% NH3 conc.) gradient from 9:1 to 8:2) to give a colorless oil. MS: 522.4 [M+H]+. tR (HPLC, Nucleosil C18HD column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 4.47 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07807709B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-78d876aa825041ada4abedfb196243d5 |
| Source note | uspto-grants-2010_10 |