Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 3,3,3-Trifluoropropanal | HCID 68028 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 4-(3-Methoxy-4-nitrophenyl)-1,2,3,6-tetrahydropyridine--hydrogen chloride (1/1) | HCID 57416165 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | HCID 67326287 | HCID 67326287 | — |
Reaction Steps
A solution of 6.6 g (24.38 mmol) of the hydrochloride prepared in step 16.1 in 110 mL of dichloromethane is cooled in an ice-water bath. 14 mL (243.8 mmol) of glacial acetic acid, 8.19 g (73.14 mmol) of 3,3,3-trifluoropropionaldehyde and 12.9 g (60.95 mmol) of sodium triacetoxyborohydride are successively added portionwise. The mixture is stirred at room temperature for 3 hours and then diluted with dichloromethane, water and aqueous 1N NaOH solution. The aqueous phase is extracted with dichloromethane and the organic phases are combined, dried over Na2SO4, filtered and concentrated under vacuum. 8.4 g of a yellow oil very predominantly containing the expected product are recovered, and are used as obtained in the following step. Quantitative crude yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08975250B2 |
|---|
| Source dataset | uspto-grants-2015_03 |
|---|
| ORD ID | ord-f6a12ddba1564f9fbe38a239ec510d89 |
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| Source note | uspto-grants-2015_03 |
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