HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 57576401, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Chloroethyl chloroformate | HCID 521305 | — |
| Reactant | HCID 67033448 | HCID 67033448 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 57576401 | HCID 57576401 | 85.4% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
To a solution of 6-{(S)-1-[(3R,4S)-1-benzyl-4-(3,4-difluoro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile—66 mg (0.16 mmol) dissolved in toluene (2 mL) were added 67 mg (0.47 mmol) of 1-chloroethyl chloroformate and 61 mg (0.47 mmol) of Hunig's base. The reaction mixture was heated at 100° C. for one hour. After cooling down to RT, volatiles were removed under vacuo and the crude was dissolved in MeOH (10 mL). The reaction mixture was heated at 85° C. for 30 minutes and after cooling down to RT, volatiles were removed under vacuo and the residue was directly purified on column chromatography (SiO2, CH2Cl2/MeOH 9:1) yielded 45 mg (85%) of the title compound as a light yellow oil. ES-MS m/e: 330.3 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394834B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-bfa77e443d6b48f694ac60137371aa79 |
| Source note | uspto-grants-2013_03 |