HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Hydroxide → (S)-4-[[[1-[(1,1-Dimethylethoxy)carbonyl]-2-pyrrolidinyl]methoxy]methyl]-1-piperidinecarboxylic acid, phenylmethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | (S)-(-)-N-Boc-prolinol | HCID 643448 | — |
| Reactant | 4-(Toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid benzyl ester | HCID 21892078 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | (S)-4-[[[1-[(1,1-Dimethylethoxy)carbonyl]-2-pyrrolidinyl]methoxy]methyl]-1-piperidinecarboxylic acid, phenylmethyl ester | HCID 131719745 | — |
Reaction Steps
To BOC-L-prolinol (10 mmol) in xylene (10 mL) was added KOH (20 mmol), 4-tosyloxymethyl-N-carbobenzyloxy piperidine (11 mmol) and the reaction was heated to reflux for 3 hours. The reaction mixture was stirred at room temperature for 16 hours, quenched with NH4Cl, extracted with ethyl acetate and purified by column chromatography to provide the title ether.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05583146 |
| Source dataset | uspto-grants-1996_12 |
| ORD ID | ord-736035f1e0ea49408516f1b7fa8f6088 |
| Source note | uspto-grants-1996_12 |