Tert-Butylamine → Tert.butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxamide

HRID 54085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 54085
[CH2:1]([O:8][C:9]([N:11]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH:12]1[C:24](O)=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:29]1CCOCC1)C.ClC(O[CH2:39][CH:40]([CH3:42])[CH3:41])=O.C(N)(C)(C)C>O1CCCC1.C(OCC)(=O)C>[C:40]([C:12]1([C:24]([NH2:29])=[O:25])[C:13]2[NH:14][C:15]3[C:20]([C:21]=2[CH2:22][CH2:23][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[CH:19][CH:18]=[CH:17][CH:16]=3)([CH3:42])([CH3:41])[CH3:39]

Komponenten

7

Edukt 4

HCID 6385Tert-ButylamineHCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 190319922-[(benzyloxy)carbonyl]-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-1-carboxylic acid

Produkt 1

HCID 86746252Tert.butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4.54 g of 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxylic acid in 45 ml of anhydrous tetrahydrofuran was cooled, while protecting with a drying tube, in an ice/acetone bath. 1.82 ml of N-ethylmorpholine and 1.82 ml of isobutyl chloroformate were added, the mixture was stirred for 10 minutes and then 2.1 ml of tert.butylamine were added. The mixture was then stirred at 0° C. for 40 minutes and at room temperature for 45 minutes, diluted with ethyl acetate and washed twice with water, twice with 0.5M sodium hydroxide solution and again with water. The solution was dried over magnesium sulphate and evaporated to dryness. Recrystallization from ethyl acetate and n-hexane gave 1.21 g of tert.butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido-[3,4-b]indole-1-carboxamide; MS: m/e 406 [M+H]+. A further 0.76 g of identical material was obtained by subjecting the mother liquors to chromatography on silica gel using ethyl acetate/n-hexane (1:1) for the elution.

Aufarbeitung

  1. customwhile protecting with a drying tube, in an ice/acetone bath
  2. stirringThe mixture was then stirred at 0° C. for 40 minutes and at room temperature for 45 minutes
  3. washwashed twice with water, twice with 0.5M sodium hydroxide solution and again with water
  4. dry with materialThe solution was dried over magnesium sulphate
  5. customevaporated to dryness
  6. customRecrystallization from ethyl acetate and n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-97266c6870b9419d80889c8b7c75b0bc
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620987

Notizen zur Reaktion

Wird geladen…