1,5-Dibromopentane → methyl(S)-3-tert-butoxycarbonylamino-2-piperidin-1-ylpropanoate

HRID 1620376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620376
C(N(CC)CC)C.Cl.[NH2:9][C@@H:10]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:11]([O:13][CH3:14])=[O:12].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br>C(O)(C)(C)C>[C:20]([O:19][C:17]([NH:16][CH2:15][C@H:10]([N:9]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:11]([O:13][CH3:14])=[O:12])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 81001,5-DibromopentaneHCID 8471TriethylamineHCID 18334328methyl (2S)-2-amino-3-{[(tert-butoxy)carbonyl]amino}propanoate hydrochloride

Produkt 1

HCID 67056335methyl(S)-3-tert-butoxycarbonylamino-2-piperidin-1-ylpropanoateAusbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

14.4 ml (104 mmol) of triethylamine are added to a solution of 8.0 g (31 mmol) of commercial methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate hydrochloride in 160 ml of tert-butanol, and then the reaction medium is stirred for 30 min at 40° C., and filtered in order to remove the triethylammonium salts. 6 ml (44 mmol) of 1,5-dibromopentane are added to the filtrate thus obtained, and the reaction medium is heated at 80° C. for 3 days. After the insoluble material has been filtered off, the filtrate is concentrated under vacuum. The crude residue is purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 5.3 g (59%) of methyl(S)-3-tert-butoxycarbonylamino-2-piperidin-1-ylpropanoate are obtained in the form of a colorless oil.

Aufarbeitung

  1. filtrationfiltered in order
  2. customto remove the triethylammonium salts
  3. customthus obtained
  4. temperaturethe reaction medium is heated at 80° C. for 3 days
  5. filtrationAfter the insoluble material has been filtered off
  6. concentrationthe filtrate is concentrated under vacuum
  7. customThe crude residue is purified by chromatography on silica gel, elution

Quellen und Nachweise

ORD-Eintrag
ord-3ae1e6cb501e411887a921d4cbe7afb6
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772478B2

Notizen zur Reaktion

Wird geladen…