Water → tert-butyl {2-[(1S,2R)-1,2-dihydroxypropyl]benzyl}carbamate

HRID 923483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923483
CS(N)(=O)=O.[OH2:6].[CH:7](/[C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:8]/[CH3:9].S([O-])([O-])(=[O:27])=S.[Na+].[Na+]>C(O)(C)(C)C>[OH:6][C@@H:7]([C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:19])[CH3:17])[C@H:8]([OH:27])[CH3:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 72879MethanesulfonamideHCID 118318066tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate

Produkt 1

HCID 118318079tert-butyl {2-[(1S,2R)-1,2-dihydroxypropyl]benzyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel2×

Versuchsvorschrift

To a mixture of 3.30 g of AD mix-α, 200 mg of methanesulfonamide, 12.5 ml of tert-butyl alcohol, and 12.5 ml of water was added a solution of 500 mg of tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate in 5 ml of tert-butyl alcohol, followed by stirring at room temperature for 12 hours. To the reaction mixture was added sodium thiosulfate, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 449 mg of tert-butyl {2-[(1S,2R)-1,2-dihydroxypropyl]benzyl}carbamate.

Aufarbeitung

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-195099e262304b24bca2d9c68b8c5fec
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278968B2

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