HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → (S)-tert-butyl 4-(3-hydroxypyrrolidin-1-yl)piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | tert-Butyl 4-oxopiperidine-1-carboxylate | HCID 735900 | — |
| Reactant | (3S)-pyrrolidin-3-ol | HCID 2733874 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-tert-butyl 4-(3-hydroxypyrrolidin-1-yl)piperidine-1-carboxylate | HCID 89618667 | 49.3% |
Reaction Steps
Acetic acid (90 mg, 1.2 mmol) was added to solution of tert-butyl 4-oxopiperidine-1-carboxylate (300 mg, 1.5 mmol) and (S)-pyrrolidin-3-ol (140 mg, 1.7 mmol) in DCE (3 mL) at 10-15° C. and stirring was continued at the same temperature for 10 minutes. Sodium triacetoxyborohydride (957 mg, 4.5 mmol) was added portionwise to the reaction mixture and stirring was continued at 20-35° C. for 16 h. The reaction mixture was diluted with DCM, washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 200 mg of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09045479B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-de16a6923ff8419998f7966c7c34c8b7 |
| Source note | uspto-grants-2015_06 |