Triphenylphosphine → ethyl[(1R)-9-[(1S)-1-(4-chlorophenyl)ethyl]-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetate

HRID 1744879

Reaktionsgleichung

Reaktionsgleichung von HRID 1744879
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]1[C:18]2[NH:17][C:16]3[C:11](=[CH:12][C:13]([F:23])=[CH:14][C:15]=3[S:19]([CH3:22])(=[O:21])=[O:20])[C:10]=2[CH2:9][CH2:8][CH2:7]1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([C@H:51](O)[CH3:52])=[CH:47][CH:46]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]1[C:18]2[N:17]([C@H:51]([C:48]3[CH:49]=[CH:50][C:45]([Cl:44])=[CH:46][CH:47]=3)[CH3:52])[C:16]3[C:11](=[CH:12][C:13]([F:23])=[CH:14][C:15]=3[S:19]([CH3:22])(=[O:21])=[O:20])[C:10]=2[CH2:9][CH2:8][CH2:7]1)[CH3:2]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 643324(1R)-1-(4-chlorophenyl)ethan-1-olHCID 91395787Ethyl[(1R)-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetate

Produkt 1

HCID 66967751ethyl[(1R)-9-[(1S)-1-(4-chlorophenyl)ethyl]-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the compound of Step 4 (1 eq), triphenylphosphine (1.5 eq) and (1R)-1-(4-chlorophenyl)ethanol (1.5 eq, prepared following the general procedure described in Reference Example 1) in THF (0.175M) was added a solution of di-tert-butyl azodicarboxylate (2.1 M in THF, 1.5 eq) over a 10 min period. The mixture was stirred at room temperature for 2 hr and concentrated. The residue was purified by silica gel flash chromatography, eluting with 7% EtOAc in toluene to give the desired product (˜90% pure) which was used as such for the next reaction.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel flash chromatography
  3. washeluting with 7% EtOAc in toluene

Quellen und Nachweise

ORD-Eintrag
ord-902882cf1c454ee5bf86cff1ff406596
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07019022B2

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