Sulfuric acid magnesium salt (1:1) → (tert-butoxy)-N-(2-{[(4-methoxyphenyl)methyl](oxolan-3-ylmethyl)amino}ethyl)carboxamide

HRID 1010545

Reaktionsgleichung

Reaktionsgleichung von HRID 1010545
[O:1]1[CH2:5][CH2:4][CH:3]([CH:6]=O)[CH2:2]1.[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].S([O-])([O-])(=O)=O.[Mg+2]>ClCCCl>[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][N:18]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH2:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Komponenten

6

Edukt 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 5049666Sodium triacetoxyborohydrideHCID 112688707Tert-butyl N-(2-{[(4-methoxyphenyl)methyl]amino}ethyl)carbamate

Produkt 1

HCID 131728997(tert-butoxy)-N-(2-{[(4-methoxyphenyl)methyl](oxolan-3-ylmethyl)amino}ethyl)carboxamideAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

This compound was made in a manner analogous to that set forth in Step D of Example 5, using 0.2 gram (0.0020 mole) of (oxolan-3-yl)formaldehyde, 0.56 gram (0.0020 mole) of (tert-butoxy)-N-(2-{[(4-methoxyphenyl)methyl]amino}-ethyl)carboxamide (prepared in Step A of Example 9), 0.64 gram (0.0030 mole) of sodium triacetoxyborohydride and 2.5 grams (0.021 mole) of magnesium sulfate in 50 mL of 1,2-dichloroethane. The reaction product was purified with column chromatography on silica gel. Elution was accomplished using a mixture of 1% methanol in methylene chloride as an eluant. Appropriate fractions were combined and concentrated under reduced pressure, yielding 0.59 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. customThe reaction product was purified with column chromatography on silica gel
  2. washElution
  3. additiona mixture of 1% methanol in methylene chloride as an eluant
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ab9d4328df8b41dcbeb9a02578764ec8
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977332B2

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