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Methanol → (4s)-5-(4-Fluorophenyl)-6-{(r)-hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropyl-2,2-di-methylchroman-4-ol

HRID 1516732
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1516732
N[C@@H]1C2C(=CC=CC=2)C[C@@H]1O.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:28]([CH:29]([OH:41])[C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)=[C:27]([CH:42]([CH3:44])[CH3:43])[CH:26]=[C:25]3[C:20]=2[C:21](=[O:47])[CH2:22][C:23]([CH3:46])([CH3:45])[O:24]3)=[CH:15][CH:14]=1.CO>O1CCCC1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:28]([C@H:29]([OH:41])[C:30]3[CH:31]=[CH:32][C:33]([O:36][C:37]([F:39])([F:40])[F:38])=[CH:34][CH:35]=3)=[C:27]([CH:42]([CH3:43])[CH3:44])[CH:26]=[C:25]3[C:20]=2[C@@H:21]([OH:47])[CH2:22][C:23]([CH3:45])([CH3:46])[O:24]3)=[CH:15][CH:14]=1
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Komponenten

5

Edukt 3

HCID 887MethanolHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 58002959Rac-5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

Produkt 1

HCID 58002982(4s)-5-(4-Fluorophenyl)-6-{(r)-hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropyl-2,2-di-methylchroman-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

140 μl (800 μmol) of borane/N,N-diethylaniline complex are added slowly to a solution of 4.45 mg (30 μmol) of (1R,2S)-1-aminoindan-2-ol in 5 ml of tetrahydrofuran. The mixture is then cooled to 0° C., and a solution of 100 mg (200 μmol) of rac-5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 24A) in 5 ml of tetrahydrofuran is then slowly added dropwise. The mixture is allowed to thaw slowly and stirred at room temperature overnight. Methanol is then added, and the solvent is removed 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. Purification of the residue by preparative HPLC (method 1) gives the diastereomerically pure target compounds.

Aufarbeitung

  1. customthe solvent is removed under reduced pressure
  2. washwashed in each case twice with 1 M hydrochloric acid and saturated sodium bicarbonate solution and once with saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by preparative HPLC (method 1)
  6. customgives the diastereomerically pure target compounds

Quellen und Nachweise

ORD-Eintrag
ord-9485932f4bd24d21a32716f9070752cd
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08227511B2

Notizen zur Reaktion

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