Methyl iodide → tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate

HRID 1374314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1374314
[C:1]([O:5][C:6](=[O:27])[NH:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C@H:10]([CH2:25][OH:26])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].I[CH3:29]>CN(C)C=O.[Ag]=O>[C:1]([O:5][C:6](=[O:27])[NH:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[C@H:10]([CH2:25][O:26][CH3:29])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 6328Methyl iodideHCID 68765914tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate

Produkt 1

HCID 68766937tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92152Silver(II) oxideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(1R,3R,4S)-(4-benzyloxycarbonylamino-3-hydroxymethyl-cyclohexyl)carbamic acid tert-butyl ester (1.8 g) was dissolved in N,N-dimethylformamide (15 mL). Iodomethane (50 mL) was added, followed by silver oxide (5.52 g), and the mixture was stirred at room temperature overnight. The mixture was filtered through Celite and the solids were washed with ethyl acetate. The filtrate was washed sequentially with water and brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography to provide (1R,3R,4S)-(4-benzyloxycarbonylamino-3-methoxymethylcyclohexyl)carbamic acid tert-butyl ester as a colorless gum (1.78 g). MS found: (M+H)+=393.

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. washthe solids were washed with ethyl acetate
  3. washThe filtrate was washed sequentially with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-23bc505903994630805796a5d390371f
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07163937B2

Notizen zur Reaktion

Wird geladen…