HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium triacetoxyborohydride → alpha-(R)-(3-(S)-((4-(5-Fluoro-benzoimidazol-1-yl)-piperidin-1-ylmethyl))-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 1-Piperidin-4-yl-5-fluoro-1-H-benzoimidazole | HCID 21193111 | — |
| Reactant | alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester | HCID 53654320 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | alpha-(R)-(3-(S)-((4-(5-Fluoro-benzoimidazol-1-yl)-piperidin-1-ylmethyl))-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester | HCID 86757026 | 73.3% |
Reaction Steps
The title compound was prepared from 40 mg of α-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester (prepared above as Aldehyde 5), 40 mg 1-piperidin-4-yl-5-fluoro-1-H-benzoimidazole (from Step C ) and 60 mg of sodium triacetoxyborohydride in 4 mL of THF and 1 mL of DMF, using a procedure analogous to that described in Example 95, Step D to provide 43 mg of the title compound as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06248755B1 |
| Source dataset | uspto-grants-2001_06 |
| ORD ID | ord-870ecb71469e44fa9ffa6f8faec9bdf1 |
| Source note | uspto-grants-2001_06 |