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Methanol → (4s)-6-(4-Tert-butylbenzyl)-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethylchroman-4-ol

HRID 1516736
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1516736
N[C@@H]1C2C(=CC=CC=2)C[C@@H]1O.[C:12]([C:16]1[CH:21]=[CH:20][C:19]([CH:22](F)[C:23]2[C:24]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)=[C:25]3[C:30](=[CH:31][C:32]=2[CH:33]([CH3:35])[CH3:34])[O:29][C:28]([CH3:37])([CH3:36])[CH2:27][C:26]3=[O:38])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].CO>O1CCCC1.C(OCC)(=O)C>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([CH2:22][C:23]2[C:24]([C:39]3[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=3)=[C:25]3[C:30](=[CH:31][C:32]=2[CH:33]([CH3:35])[CH3:34])[O:29][C:28]([CH3:36])([CH3:37])[CH2:27][C@@H:26]3[OH:38])=[CH:20][CH:21]=1)([CH3:14])([CH3:15])[CH3:13]
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Komponenten

6

Edukt 3

HCID 887MethanolHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 58003037Rac-6-[(4-tert-butylphenyl)(fluoro)methyl]-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

Produkt 1

HCID 58002952(4s)-6-(4-Tert-butylbenzyl)-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethylchroman-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

150 μl (840 μmol) of borane/N,N-diethylaniline complex are added slowly to a solution of 4.70 mg (30 μmol) of (1R,2S)-1-aminoindan-2-ol in 5 ml of tetrahydrofuran, and the mixture is stirred for 30 min. A solution of 100 mg (210 μmol) of rac-6-[(4-tert-butylphenyl)(fluoro)methyl]-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 28A) in 5 ml of tetrahydrofuran is then slowly added dropwise. After 3 h of stirring at room temperature, methanol is added and the solvent is reduced 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 column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 10:1→5:1) gives the target product.

Aufarbeitung

  1. stirringAfter 3 h of stirring at room temperature
  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 column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 10:1→5:1)
  6. customgives the target product

Quellen und Nachweise

ORD-Eintrag
ord-3d03d7c73640452b9d3d2fe7c7798b5d
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08227511B2

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