HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonyl chloride → HCID 11151879, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | (2R,4S)-N-Boc-4-Hydroxypiperidine-2-Carboxylic Acid Methyl Ester | HCID 2734504 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 11151879 | HCID 11151879 | 98% |
Reaction Steps
MsCl (6.61 mL, 85 mmol) was added dropwise at 0° C. to a solution of (2R,4S)-1-tert-butyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate (21 g, 81 mmol) and DMAP (100 mg, 0.81 mmol) in pyridine (50 mL). The mixture was stirred at room temperature for 5 hours and then was concentrated under reduced pressure to remove most solvent. Brine (200 mL) was added and extracted with ethyl acetate (2×200 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give title compound 26.7 g (98%) as colorless oil. LC-MS: 338.1 (t=1.9 min).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08148401B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-ad6b31a6d6db438191c3a6d5d1f4820c |
| Source note | uspto-grants-2012_04 |