Ethyl Acetate → (2S,3S)-3-(dibenzylamino)-2-hydroxyhexanenitrile

HRID 1972327

Reaktionsgleichung

[CH2:1]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@@H:9]([CH2:12][CH2:13][CH3:14])[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(O)[O-].[Na+].[C-:27]#[N:28].[Na+].C(OCC)(=O)C>CO.O.C(OCC)(=O)C.CCCCCC>[CH2:15]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]([CH2:12][CH2:13][CH3:14])[C@H:10]([OH:11])[C:27]#[N:28])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

Reaktionsbedingungen

Temperatur: 2.5 °C

Versuchsvorschrift

To a solution of (S)-2-(dibenzylamino)pentanal (125 g; 0.444 mol) in methanol (375 mL) at 0-5° C. was added a previously cooled (0-5° C.) aqueous solution of sodium bisulfite (69.39 g, 0.667 mol; 150 mole %) in water (530 mL). The reaction mixture was stirred at 0-5° C. for 14 hours. A solution of sodium cyanide (32.02 g; 0.667 mol; 150 mol %) in water (402 mL), followed by ethyl acetate (1.25 L) was added to the above reaction mixture at 0° C. Stirring was continued at ambient temperature for 5 hours, monitoring progress of the reaction by TLC analysis (ethyl acetate/hexane, 1:9). Once the reaction was complete, the ethyl acetate layer was separated, washed with water (2×750 mL) and dried over sodium sulfate. The organic extract was concentrated under reduced pressure, washed with hexanes (200 mL), to provide 94 g of crude product as an off-white solid.

Aufarbeitung

additionwas added to the above reaction mixture at 0° C
stirringStirring
waitwas continued at ambient temperature for 5 hours
customthe ethyl acetate layer was separated
washwashed with water (2×750 mL)
dry with materialdried over sodium sulfate
extractionThe organic extract
concentrationwas concentrated under reduced pressure
washwashed with hexanes (200 mL)

Quellen und Nachweise

ORD-Eintrag: ord-3dc89adeaadc425eafffe0285d377cb8
Quelldatensatz: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08431733B2

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