N,N-Dimethylglycine → (S)-4-[4-(4-benzylphenoxy)-benzyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

HRID 1669517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669517
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([C:30]1[CH:35]=[CH:34][C:33](I)=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.ClCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:33]3[CH:34]=[CH:35][C:30]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:31][CH:32]=3)=[CH:18][CH:19]=2)[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 27593641-Benzyl-4-iodobenzeneHCID 10425336tert-Butyl (S)-4-(4-hydroxybenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Produkt 1

HCID 67353048(S)-4-[4-(4-benzylphenoxy)-benzyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl esterAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-4-(4-Hydroxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (240 mg, 0.75 mmol, 1 eq. obtained from Brian Bock, Lot No: MCLS1172-077-1), 4-benzyliodobenzene (294 mg, 1 mmol, 1.3 eq.) in dioxane (4 ml) was added CuI(I) (30 mg, 0.75 mmol, 0.1 eq.), N,N-dimethylglycine (45 mg, 0.23 mmol, 0.3 eq.) and cesium carbonate (500 mg, 1.5 mmol, 3 eq.). The resulting mixture was stirred under Ar at reflux overnight. After cooling to room temperature, the volatile material was removed under reduced pressure to give a residue, which was partitioned between water (10 ml) and ethyl acetate (10 ml). The ethyl acetate layer was separated and dried over anhydrous MgSO4. Evaporation of solvent under reduced pressure gave a residue, which was passed through a plug of silica gel using dichloromethane (50 ml) as eluent to give 350 mg of desired product containing the starting iodide, which was forwarded to the next step without further purification.

Aufarbeitung

  1. temperatureat reflux overnight
  2. customthe volatile material was removed under reduced pressure
  3. customto give a residue, which
  4. customwas partitioned between water (10 ml) and ethyl acetate (10 ml)
  5. customThe ethyl acetate layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. customEvaporation of solvent under reduced pressure
  8. customgave a residue, which

Quellen und Nachweise

ORD-Eintrag
ord-46b59a4272d94d38849b150b58e4a4ab
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989480B2

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