Potassium Bromide → N-butyl-2-((4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

HRID 877945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877945
[CH2:1]([NH:5][C:6](=[O:18])[CH2:7][C@H:8]1[CH2:13][C@@H:12]([CH2:14][OH:15])[O:11][C:10]([CH3:17])([CH3:16])[O:9]1)[CH2:2][CH2:3][CH3:4].CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].Cl[O-].[Na+]>C(Cl)Cl>[CH2:1]([NH:5][C:6](=[O:18])[CH2:7][C@H:8]1[CH2:13][C@@H:12]([CH:14]=[O:15])[O:11][C:10]([CH3:17])([CH3:16])[O:9]1)[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 253877Potassium BromideHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 53339170N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

Produkt 1

HCID 24826227N-butyl-2-((4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl) acetamide (6 grams) in methylene chloride (24 ml) was added to a pre-cooled mixture of TEMPO (0.01 gram), methylene chloride (36 ml) and potassium bromide (0.26 grams) at −5 to −15° C. Sodium hypo chlorite (15.6 ml) was added to the reaction mixture at −15 to −5° C. and stirred. After completion of the reaction, quenched it with 10% sodium thio sulfate solution at room temperature and water was added to it. Both organic and aqueous layers were separated and organic layer was washed with water followed by saturated sodium chloride solution. The solvent from organic layer was distilled off under reduced pressure to get the title compound.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customquenched it with 10% sodium thio sulfate solution at room temperature
  3. additionwater was added to it
  4. customBoth organic and aqueous layers were separated
  5. washorganic layer was washed with water
  6. distillationThe solvent from organic layer was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0ba0adec03ac4a669bd0b4953a7f5230
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987444B2

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