3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → HCID 68809159, Verbindung

HRID 434299

Reaktionsgleichung

Reaktionsgleichung von HRID 434299
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]=O)[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:25])=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][N:29]2[CH2:30][CH2:31][CH:26]([C:24](=[O:25])[C:21]3[CH:20]=[CH:19][C:18]([Cl:17])=[CH:23][CH:22]=3)[CH2:27][CH2:28]2)[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-HCID 27771154-(4-Chlorobenzoyl)PiperidineHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 68809159HCID 68809159, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (R)4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.5 g, 2.18 mmol) in tetrahydrofuran (15 ml) is added (4-chloro-phenyl)-piperidin-4-yl-methanone (0.49 g, 2.18 mmol) and sodium triacetoxyborohydride (0.69 g, 3.27 mmol), and the reaction mixture stirred for 3.5 hours at ambient temperature. The solvent is evaporated and the residue partitioned between ethyl acetate (50 ml) and saturated sodium bicarbonate solution (50 ml). The ethyl acetate is dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (ethyl acetate:hexane, 1:1 elution) to afford (S)-4-[4-(4-chloro-benzoyl)-piperidin-1-ylmethyl]-2,2-dimethyl-oxazoldine-3-carboxylic acid tert-butyl ester, [MH]+437.2.

Aufarbeitung

  1. customThe solvent is evaporated
  2. customthe residue partitioned between ethyl acetate (50 ml) and saturated sodium bicarbonate solution (50 ml)
  3. dry with materialThe ethyl acetate is dried over magnesium sulphate
  4. customevaporated
  5. customThe crude product is purified by flash silica chromatography (ethyl acetate:hexane, 1:1 elution)

Quellen und Nachweise

ORD-Eintrag
ord-289e5a0a2c844c5689bd9fe851d1b3ea
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06670379B2

Verknüpfte Notizen

Wird geladen…