Triethylamine → 4-Methyl-4-(p-nitrobenzyloxycarbonyl)aminopentanol

HRID 1252225

Reaktionsgleichung

Reaktionsgleichung von HRID 1252225
[CH3:1][C:2]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:11])([CH3:8])[CH2:3][CH2:4][C:5](O)=[O:6].C(N(CC)CC)C.ClC(OCC)=O>O1CCCC1>[CH3:8][C:2]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=1)=[O:11])([CH3:1])[CH2:3][CH2:4][CH2:5][OH:6]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 133343844-Methyl-4-(p-nitrobenzyloxycarbonyl)aminovaleric acid

Produkt 1

HCID 201408004-Methyl-4-(p-nitrobenzyloxycarbonyl)aminopentanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 4-methyl-4-(p-nitrobenzyloxycarbonyl)aminovaleric acid (14.0 g) and triethylamine (5.25 g) in tetrahydrofuran (280 ml), ethyl chloroformate (5.64 g) was added with ice-cooling and then stirred for 30 minutes. The resulting triethylamine hydrochloride was removed by filtration. To filtrate was added sodium borohydride (5 g) in water (90 mg) with ice-cooling, and the mixture was stirred for 1.5 hours. The reaction mixture was concentrated to a volume of 120 ml in vacuo and extracted with dichloromethane. The dichloromethane layer was washed with diluted hydrochloric acid and then water, dried over anhydrous sodium sulfate and evaporated in vacuo to give an oily residue which was then purified by silica gel chromatography to give 4-methyl-4-(p-nitrobenzyloxycarbonyl)aminopentanol.

Aufarbeitung

  1. additionwas added with ice-
  2. temperaturecooling
  3. customThe resulting triethylamine hydrochloride was removed by filtration
  4. additionTo filtrate was added sodium borohydride (5 g) in water (90 mg) with ice-
  5. temperaturecooling
  6. stirringthe mixture was stirred for 1.5 hours
  7. concentrationThe reaction mixture was concentrated to a volume of 120 ml in vacuo
  8. extractionextracted with dichloromethane
  9. washThe dichloromethane layer was washed with diluted hydrochloric acid
  10. dry with materialwater, dried over anhydrous sodium sulfate
  11. customevaporated in vacuo
  12. customto give an oily residue which
  13. customwas then purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aeb5bb4dba7b42c5bfeaebee6c17486c
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04742052

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