HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanamine, N-methoxy-, hydrochloride (1:1) → Tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acid | HCID 2755965 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate | HCID 57449675 | — |
Reaction Steps
To a stirred solution of (±)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (1.51 g, 6.53 mmol), N,O-dimethylhydroxylamine hydrochloride (0.83 g, 8.49 mmol) and i-Pr2NEt (3.1 mL, 17.6 mmol) in CH2Cl2 (30 mL) was added solid HATU (3.01 g, 7.85 mmol). The mixture was stirred at rt for 3 d, diluted with ether (175 mL), washed with 5% aq HCl (2×50 mL) and satd aq NaHCO3 (50 mL) and dried over MgSO4. Removal of the solvent left (±)-tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate (1.73 g, 96%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07754737B2 |
| Source dataset | uspto-grants-2010_07 |
| ORD ID | ord-ce1eb844de0f425bb489551ea2bb23db |
| Source note | uspto-grants-2010_07 |