Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 68451900 | HCID 68451900 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 68450887 | HCID 68450887 | 96.7% |
Reaction Steps
The compound (171 mg) obtained in Example 17 was suspended in methylene chloride (10 mL), and triethylamine (0.104 mL) was added, followed by stirring at room temperature for 10 minutes. After acetic acid (0.059 mL) was added to the reaction mixture, a 35% formalin (0.070 mL) and sodium triacetoxyborohydride (118 mg) were added, and the mixture was stirred at room temperature for 30 minutes. After 1N aqueous sodium hydroxide (3 mL) was added to the reaction mixture, water was added for partitioning the mixture. After the resultant organic layer was dried over sodium sulfate anhydrate, the solvent was then distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=50:3) to give a colorless foamy substance. This substance was suspended in 1N hydrochloric acid, and the suspension was concentrated under reduced pressure to give the title compound (85 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07576135B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-5eaa720e28594b56a93b91d82c94ff04 |
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| Source note | uspto-grants-2009_08 |
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