HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,1-Dichloroethane → HCID 57672054, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,1-Dichloroethane | HCID 6365 | — |
| Reactant | N-Aminomorpholine | HCID 20315 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | (R)-4-((R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde | HCID 59515429 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57672054 | HCID 57672054 | 80% |
Reaction Steps
Stir a mixture of dichloroethane (25 mL), N-aminomorpholine (0.204 g, 2 mmol), (R)-4-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde (1.064 g, 2 mmol) and sodium triacetoxyborohydride (1.266 g, 6 mmol) at room temperature for 12 hours. Bring the reaction to 60° C. and stir for 3 hours. Cool the reaction, dilute with dichloromethane, and wash with water. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify on silica with a 50 to 75% ethyl acetate in hexanes gradient to afford 0.07 g (80%) of the titled product. MS (m/z): 435 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08153807B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-c65aac406fc943e28ad45bcc4ad03401 |
| Source note | uspto-grants-2012_04 |