Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Cyano-borohydride | HCID 498716 | — |
| Reactant | (1-Ethoxycyclopropoxy)trimethylsilane | HCID 2734686 | — |
| Reactant | HCID 68750976 | HCID 68750976 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 68750968 | HCID 68750968 | 66.1% |
Reaction Steps
Solid supported cyanoborohydride (2.5 mmol/g, 46 mg) was added to a solution of 4-fluoro-N-[2-fluoro-5-(1-trityl-1H-benzotriazol-5-yl)-benzyl]-N-piperidin-4-yl-benzamide (20 mg, 0.029 mmol), (1-ethoxy-cyclopropoxy)-trimethylsilane (25 mg, 0.145 mmol) and acetic acid (1.74 mg, 0.029 mmol) in 1 mL of methanol. The mixture was stirred at 45° C. for 2 h and then at 75° C. overnight. The mixture was cooled and filtered and the filtrate concentrated in vacuo to provide the crude product. Chromatography provided 14 mg of product. LC/MS: Retention time, 3.20 min; (M+H)=730.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07625889B2 |
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| Source dataset | uspto-grants-2009_12 |
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| ORD ID | ord-36ba7011e17e4969958dc0a72a5c1496 |
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| Source note | uspto-grants-2009_12 |
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