Methanol → Rac-5-cyclopent-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

HRID 1516709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516709
N[C@@H]1C2C(=CC=CC=2)C[C@@H]1O.[C:12]1([C:17]2[C:26]([CH:27]([OH:38])[C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)=[C:25]([CH:39]([CH3:41])[CH3:40])[CH:24]=[C:23]3[C:18]=2[C:19](=[O:44])[CH2:20][C:21]([CH3:43])([CH3:42])[O:22]3)[CH2:16][CH2:15][CH2:14][CH:13]=1.CO>O1CCCC1>[CH:12]1([C:17]2[C:26]([CH:27]([OH:38])[C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:30][CH:29]=3)=[C:25]([CH:39]([CH3:40])[CH3:41])[CH:24]=[C:23]3[C:18]=2[C:19](=[O:44])[CH2:20][C:21]([CH3:42])([CH3:43])[O:22]3)[CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 58002986Rac-5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

Produkt 1

HCID 58002966Rac-5-cyclopent-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

155 μl (872 μmol) of borane/N,N-diethylaniline complex are added slowly to a solution of 4.9 mg (33 μmol) of (1R,2S)-1-aminoindan-2-ol in 5.0 ml of tetrahydrofuran, and the mixture is stirred for 30 min. A solution of 100 mg (218 μmol) of 5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 36A) in 5.0 ml of tetrahydrofuran is then, very slowly, added dropwise, and the mixture is stirred for 4 h. Methanol is then added, and the mixture is concentrated under reduced pressure. The residue is taken up in ethyl acetate and washed in each case twice with 1 M hydrochloric acid and saturated sodium bicarbonate solution and once with saturated sodium chloride solution. The organic phase is dried over sodium sulfate and then concentrated under reduced pressure. The crude product is purified by preparative HPLC (method 1). In addition to the title compound, the compounds described as Preparation Examples 22 and 23 are also isolated (for yield and analytical data see there).

Aufarbeitung

  1. additionvery slowly, added dropwise
  2. stirringthe mixture is stirred for 4 h
  3. concentrationthe mixture is concentrated under reduced pressure
  4. washwashed in each case twice with 1 M hydrochloric acid and saturated sodium bicarbonate solution and once with saturated sodium chloride solution
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by preparative HPLC (method 1)
  8. additionIn addition to the title compound
  9. customthe compounds described as Preparation Examples 22 and 23
  10. customare also isolated (
  11. customfor yield

Quellen und Nachweise

ORD-Eintrag
ord-148035b1eef24b2d8a810749193fd6ca
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227511B2

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