HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium triacetoxyborohydride → alpha-(r)-(3-(s)-((4-(2-Methyl-benzoimidazol-1-yl)piperidin-1-yl)methyl)-4-(s)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 2-Methyl-1-(4-piperidinyl)-1H-benzimidazole | HCID 12961849 | — |
| 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-(2-Methyl-benzoimidazol-1-yl)piperidin-1-yl)methyl)-4-(s)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester | HCID 57317010 | 69.8% |
Reaction Steps
The title compound was prepared from 60 mg of α-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester (prepared above as Aldehyde 5), 50 mg of 1-1-piperidin-4-yl-2-methyl-1-H-benzoimidazole (from Step B) and 80 mg of sodium triacetoxyborohydride in 4 mL THF and 1 mL of DMF, using a procedure analogous to that described in Example 95, Step D to provide 61 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-565cf0229f924a86a0ef0913b6d49c93 |
| Source note | uspto-grants-2001_06 |