HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → Ammonia
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | (3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine | HCID 1514397 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Solvent | Formaldehyde | HCID 712 | — |
| Product | Ammonia | HCID 222 | 2.5% |
| Product | (R)-tert-Butyl 1-methylpyrrolidin-3-ylcarbamate | HCID 45091942 | — |
Reaction Steps
(3R)-3-(Bocamino)pyrrolidine (Fluorochem; 2.5 g, 13.42 mmol) was dissolved in 37% aqueous formaldehyde (78 mL) and acetic acid (8.5 mL, 134.23 mmol). Sodium acetate (11.0 g, 134.23 mmol) was added and the mixture cooled in an ice/water bath. Sodium cyanoborohydride (844 mg, 13.42 mmol) was added and the mixture allowed to stir for 3 hours. Saturated aqueous sodium hydrogen carbonate was added until the mixture was basic. The mixture was extracted with DCM (×2) and the combined extracts dried (MgSO4) and concentrated. Column chromatography (2.5-5% 7N ammonia in methanol) yielded the title compound as a colourless liquid that crystallised on standing (1.20 g, 45%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07709471B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-f94826acfdf14999b01f609e3684f34a |
| Source note | uspto-grants-2010_05 |