Triethylamine → Tert-butyl trans-4-(N-methoxy-N-methylcarbamoyl)cyclohexylcarbamate

HRID 29758

Reaktionsgleichung

Reaktionsgleichung von HRID 29758
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][NH:20][CH3:21].C1CCC(N=C=NC2CCCCC2)CC1.C(N(CC)CC)C>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][CH:12]([C:15](=[O:17])[N:20]([O:19][CH3:18])[CH3:21])[CH2:13][CH2:14]1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 14232N,O-DimethylhydroxylamineHCID 27559964-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

Produkt 1

HCID 24720928Tert-butyl trans-4-(N-methoxy-N-methylcarbamoyl)cyclohexylcarbamateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-[N-(tert-butoxycarbonyl)amino]-cyclohexane carboxylic acid (11.95 g, 49.0 mmol), O,N-dimethylhydroxylamine (4.88 g, 50.0 mmol), DCC (9.60 g, 50 mmol) and triethylamine (5.06 g, 50.0 mmol) in DMF (150 mL) was stirred at room temperature overnight. Water (500 mL) was added and the mixture was extracted with CHCl3. The organic phase was washed with water, dried and concentrated under reduced pressure. Purification by flash chromatography (hexane/EtOAc 1:1) gave [4-(methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester (8.50 g, 61%).

Aufarbeitung

  1. extractionthe mixture was extracted with CHCl3
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (hexane/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c7af7f81ca4e42c0a273fa448c39b0b8
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423012B2

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