Pyridine → (S)-tert-butyl 3-(acetamidomethyl)morpholine-4-carboxylate

HRID 1771208

Reaktionsgleichung

Reaktionsgleichung von HRID 1771208
[NH2:1][CH2:2][C@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].N1C=CC=CC=1.[C:22](Cl)(=[O:24])[CH3:23]>ClCCl.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>[C:22]([NH:1][CH2:2][C@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=[O:24])[CH3:23]

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 44182324(S)-tert-Butyl 3-(aminomethyl)morpholine-4-carboxylate

Produkt 1

HCID 66723613(S)-tert-butyl 3-(acetamidomethyl)morpholine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5234Sodium ChlorideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of (S)-tert-butyl 3-(aminomethyl)morpholine-4-carboxylate (commercially available, 0.62 g, 2.87 mmol) in dichloromethane (28.0 ml) were added sequentially pyridine (0.5 ml, 5.73 mmol) and acetyl chloride (0.25 ml, 3.44 mmol). After 30 min the reaction was diluted with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The resulting mixture was extracted with ethyl acetate (×3), and the combined organic layers were then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting light yellow oil was purified by flash column chromatography (ISCO, SiO2, 0→10% methanol in ethyl acetate over 10 min) to afford (S)-tert-butyl 3-(acetamidomethyl)morpholine-4-carboxylate (0.741 g, yield: almost quantitative, INTERMEDIATE 86A STEP 1).

Aufarbeitung

  1. extractionThe resulting mixture was extracted with ethyl acetate (×3)
  2. dry with materialthe combined organic layers were then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting light yellow oil was purified by flash column chromatography (ISCO, SiO2, 0→10% methanol in ethyl acetate over 10 min)

Quellen und Nachweise

ORD-Eintrag
ord-9ff96de23ff84d01a6b5490e1521df03
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09248140B2

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