HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methylamine → Tert-butyl 2-(methylcarbamoyl)morpholine-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methylamine | HCID 6329 | — |
| 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 | Ethanol | HCID 702 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-butyl 2-(methylcarbamoyl)morpholine-4-carboxylate | HCID 66760938 | — |
Reaction Steps
To a cold solution (ice bath) of N-Boc-2-morpholinecarboxylic acid (0.5 g, 2.16 mmol) in DMF (10 mL) was added HATU ((2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) (0.98 g, 2.58 mmol), N,N diisopropylethylamine (2.2 g, 17.3 mmol), and 1 mL of 8 N solution of methylamine in ethanol. After the addition was finished the ice bath was removed, and the heterogeneous solution was stirred overnight at room temperature. The solution was dissolved in ethyl acetate (50 mL) and washed with a saturated solution of NaHCO3. Ethyl acetate layer was separated, dried (MgSO4) and concentrated under reduced pressure to give tert-butyl 2-(methylcarbamoyl)morpholine-4-carboxylate as an oil. MS (APCI) 245 (M+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08252793B2 |
| Source dataset | uspto-grants-2012_08 |
| ORD ID | ord-57c2ddf0d62245dfb2832681d705e999 |
| Source note | uspto-grants-2012_08 |