StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

N-(3-{[2-((1S,2S)-6-Fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-ethyl]-methyl-amino}-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide → (1S,2S)-6-fluoro-1-isopropyl-2-(2-{[3-(3-methoxy-2-methoxymethyl-2-methyl-propylamino)-propyl]-methyl-amino}-ethyl)-1,2,3,4-tetrahydro-naphthalen-2-ol

HRID 2090570
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2090570
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([CH:12]([CH3:14])[CH3:13])[C@:7]([CH2:16][CH2:17][N:18]([CH3:33])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=O)[C:24]([CH2:29][O:30][CH3:31])([CH3:28])[CH2:25][O:26][CH3:27])([OH:15])[CH2:6][CH2:5]2>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([CH:12]([CH3:14])[CH3:13])[C@:7]([CH2:16][CH2:17][N:18]([CH2:19][CH2:20][CH2:21][NH:22][CH2:23][C:24]([CH2:25][O:26][CH3:27])([CH3:28])[CH2:29][O:30][CH3:31])[CH3:33])([OH:15])[CH2:6][CH2:5]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

3

Edukt 1

HCID 67337793N-(3-{[2-((1S,2S)-6-Fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-ethyl]-methyl-amino}-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide

Produkt 1

HCID 67337353(1S,2S)-6-fluoro-1-isopropyl-2-(2-{[3-(3-methoxy-2-methoxymethyl-2-methyl-propylamino)-propyl]-methyl-amino}-ethyl)-1,2,3,4-tetrahydro-naphthalen-2-olAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 4.09 g of N-(3-{[2-((1S,2S)-6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-ethyl]-methyl-amino}-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide in anh. THF (70 mL) was added dropwise at 0° C. for 15 min a 1M solution of borane-THF complex in THF (87 mL). The mixture was stirred for 25 min at rt then for 1.5 h at 65° C. It was cooled down to 0° C., quenched with 1M-NaOH and extracted with DCM. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude as borane complex was dissolved in MeOH (60 mL) and treated with ethylene diamine (2.37 mL) under microwave conditions (120° C. for 180 s). The mixture was concentrated in vacuo and the resulting residue was taken up in DCM. The organic phase was washed with brine, dried over anh. Na2SO4 and concentrated in vacuo. The oily crude was purified by CC using EtOAc/MeOH/NEt3 from 95/5/1 to 60/40/1 as eluant to yield 2.74 g of (1S,2S)-6-fluoro-1-isopropyl-2-(2-{[3-(3-methoxy-2-methoxymethyl-2-methyl-propylamino)-propyl]-methyl-amino}-ethyl)-1,2,3,4-tetrahydro-naphthalen-2-ol as yellowish oil.

Aufarbeitung

  1. waitfor 1.5 h at 65° C
  2. temperatureIt was cooled down to 0° C.
  3. customquenched with 1M-NaOH
  4. extractionextracted with DCM
  5. dry with materialThe organic phase was dried over anh. Na2SO4
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resulting crude as borane complex was dissolved in MeOH (60 mL)
  8. additiontreated with ethylene diamine (2.37 mL) under microwave conditions (120° C. for 180 s)
  9. concentrationThe mixture was concentrated in vacuo
  10. washThe organic phase was washed with brine
  11. dry with materialdried over anh. Na2SO4
  12. concentrationconcentrated in vacuo
  13. customThe oily crude was purified by CC

Quellen und Nachweise

ORD-Eintrag
ord-244c14a2d5ff4fa4b06cde8d3fa2392f
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08436205B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion