Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 4-(Trifluoromethyl)benzaldehyde | HCID 67996 | — |
| Reactant | 2-Amino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol | HCID 54358865 | — |
| Reactant | HCID 178511851 | HCID 178511851 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 53870183 | HCID 53870183 | 83.6% |
Reaction Steps
In methanol (20 ml) were dissolved 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.5 g) obtained in Example 1 (2) and 4-trifluoromethylbenzaldehyde (0.28 g). To the solution were added acetic acid (0.1 g) and cyano sodium borohydride (0.17 g). The mixture was stirred for 40 minutes at 60° C. The reaction mixture was concentrated, to which were added ethyl acetate (30 ml) and water (20 ml), followed by extraction. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give 5-chloro-2-(4-trifluoromethylbenzylamino)-α-(3-tert-b-utoxycarbonylaminomethylphenyl)benzyl alcohol (0.6 g) as a colorless oily product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06352982B1 |
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| Source dataset | uspto-grants-2002_03 |
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| ORD ID | ord-90a748589c9243b386e93c9e6cfeb13c |
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| Source note | uspto-grants-2002_03 |
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