HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → (1S,2R) N-[3-[3-Bromo-5-(2,2-dimethyl-propyl)-benzylamino]-1-(3,5-difluoro-benzyl)-2-hydroxy-propyl]-acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | dibromobenzylamine (1S,2R)N-[3-(2,5-Dibromo-benzylamino)-1-(3,5-difluoro-benzyl)-2-hydroxy-propyl]-acetamide | HCID 86617022 | — |
| Reactant | HCID 178445888 | HCID 178445888 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (1S,2R) N-[3-[3-Bromo-5-(2,2-dimethyl-propyl)-benzylamino]-1-(3,5-difluoro-benzyl)-2-hydroxy-propyl]-acetamide | HCID 58909250 | — |
Reaction Steps
To dibromobenzylamine (1S,2R) N-[3-(2,5-Dibromo-benzylamino)-1-(3,5-difluoro-benzyl)-2-hydroxy-propyl]-acetamide (0.504 g, 1.0 mM, 1 eq) was added 0.5 M THF solution of neopentylzinc iodide (20 mL, 10 eq) and 0.082 g, (0.1 mM, 0.1 eq) of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (Pd(dppf)Cl2 CH2Cl2). A reaction mixture was stirred overnight at room temperature. The reaction was quenched with a saturated aqueous solution of NH4Cl (20 mL) and extracted with ethyl acetate (3×30 mL). Combined organic layers were washed with brine, dried and concentrated.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07645780B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-81870eeb4a2e4726be7c6fb473e863d5 |
| Source note | uspto-grants-2010_01 |