HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3(S)-(2,3-Dihydro-benzofuran-6-yl)-3-(3-[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-2-oxo-pyrrolidin-1-yl)-propionic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 3(S)-Amino-3-(2,3-dihydro-benzofuran-6-yl)-propionic acid ethyl ester | HCID 10823646 | — |
| Reactant | 6-(2-Methyl-[1,3]dioxolan-2-yl)-3-(2-oxo-oxazolidine-3-carbonyl)-hexanal | HCID 15453759 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3(S)-(2,3-Dihydro-benzofuran-6-yl)-3-(3-[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-2-oxo-pyrrolidin-1-yl)-propionic acid ethyl ester | HCID 15453768 | — |
Reaction Steps
A mixture of 2-5 (440 mg, 1.6 mmol), 3-6 (400 mg, 1.5 mmol), Na(OAc)3BH (469 mg, 2.25 mmol) and NEt3 (0.41 mL, 3.0 mmol) in dichloroethane (10 mL) was stirred for 48 h. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 50:35:14:1 hexanes/chloroform/ethyl acetate/MeOH) to give 4-1 as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06268378B1 |
| Source dataset | uspto-grants-2001_07 |
| ORD ID | ord-186013b0eeec4202bdbac8f17321ef6e |
| Source note | uspto-grants-2001_07 |