HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl morpholine oxide → (2S,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-(1-hydroxyethyl)pyrrolidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl morpholine oxide | HCID 82029 | — |
| Reactant | (2R,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-(1-hydroxyethyl)pyrrolidine | HCID 59734597 | — |
| Catalyst | HCID 178419074 | HCID 178419074 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | (2S,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-(1-hydroxyethyl)pyrrolidine | HCID 66863428 | — |
Reaction Steps
To intermediate 14A (0.1M solution in 10% CH3CN in DCM) add NMO (2 eq) followed by TPAP (0.05 eq). Provide sufficient ventilation and take care to watch for exotherm. Stir reaction at rt for 3-5 h. Dilute by half with hexane and allow TPAP to precipitate. Flash filter through silica gel plug (20 fold mass of starting alcohol) and elute with 10% EtOAc/Hex until product is not observed in eluent. Removal of solvents gave the title compound. MS (ES) m/z 344.31 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07625923B2 |
| Source dataset | uspto-grants-2009_12 |
| ORD ID | ord-d2a64e11e0084522b169aaa73110582a |
| Source note | uspto-grants-2009_12 |