Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Acetaldehyde | HCID 177 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 153624-15-8 | HCID 9908909 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 10741151 | HCID 10741151 | 53% |
Reaction Steps
To a solution of the compound of Example 32 (0.16 g, 0.4 mmol) and acetic acid (0.06 g, 1 mmol) in dichloroethane (2.5 mL) at 0° C., acetaldehyde (24 mg, 0.55 mmol) and sodium triacetoxyborohydride (212 mg, 1 mmol) were added. The mixture was stirred at 0-15° C. for 2 hours, diluted with ethyl acetate, extracted with water and brine, dried and concentrated. The residue was chromatographed on silica gel with 4:1 hexanes/ethyl acetate to afford the title compound (90 mg, 53%) as a light yellow gum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06107320 |
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| Source dataset | uspto-grants-2000_08 |
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| ORD ID | ord-768e658e3a174e508b9a4fa8c7249227 |
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| Source note | uspto-grants-2000_08 |
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