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2,2,2-Trifluoroethyl formate → methyl(7R)-14-cyclohexyl-7-{methyl[3-(methylamino)propyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 421940
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 421940
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:35])[C@@H:6]1[CH2:13][N:12]2[C:14]3[CH:15]=[C:16]([C:27]([O:29][CH3:30])=[O:28])[CH:17]=[CH:18][C:19]=3[C:20]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[C:11]2[C:10]2[CH:31]=[CH:32][CH:33]=[CH:34][C:9]=2[O:8][CH2:7]1.[CH:36](OCC(F)(F)F)=O>C1COCC1>[CH:21]1([C:20]2[C:19]3[CH:18]=[CH:17][C:16]([C:27]([O:29][CH3:30])=[O:28])=[CH:15][C:14]=3[N:12]3[C:11]=2[C:10]2[CH:31]=[CH:32][CH:33]=[CH:34][C:9]=2[O:8][CH2:7][C@H:6]([N:5]([CH3:35])[CH2:4][CH2:3][CH2:2][NH:1][CH3:36])[CH2:13]3)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1
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Komponenten

4

Edukt 2

HCID 1416812,2,2-Trifluoroethyl formateHCID 66674629methyl(7R)-7-[(3-aminopropyl)(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Produkt 1

HCID 66674033methyl(7R)-14-cyclohexyl-7-{methyl[3-(methylamino)propyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of methyl(7R)-7-[(3-aminopropyl)(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.16 M) in THF was treated dropwise with 2,2,2-trifluoroethyl formate (1.3 eq.) and stirred overnight at RT. The volatiles were removed in vacuo and the residue dissolved (0.08 M) in THF and treated dropwise with BH3-DMS complex (2 M in THF; 10 eq.). The resulting solution was stirred at RT for 3 h. The reaction was quenched by the careful addition of HCl/MeOH (1.25 M) and the resulting solution refluxed for 2 h. The volatiles were then removed in vacuo and the residue partitioned between sat. aq. NaHCO3 and EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude material was purified by FC (EtOAc/MeOH/Et3N 90:8:2) affording the product as a pale orange solid (80% overall for steps 2, 3, 4, 5). (ES) m/z 490 (M+H)+.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue dissolved (0.08 M) in THF
  3. stirringThe resulting solution was stirred at RT for 3 h
  4. customThe reaction was quenched by the careful addition of HCl/MeOH (1.25 M)
  5. temperaturethe resulting solution refluxed for 2 h
  6. customThe volatiles were then removed in vacuo
  7. customthe residue partitioned between sat. aq. NaHCO3 and EtOAc
  8. washThe combined organics were washed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude material was purified by FC (EtOAc/MeOH/Et3N 90:8:2)

Quellen und Nachweise

ORD-Eintrag
ord-161ee7ed0e064ab0aab92f958658f74b
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08101595B2

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