Dichloromethane → (3aR,7R,7aR)-2-{[2-(3-dimethylaminopropoxy)phenyl]acetyl}-4,4-diphenyl-7-fluoroperhydroisoindole hydrochloride

HRID 2399991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2399991
CN(C)CCCN=C=NCC.[C:12]1([C:18]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:26][CH2:25][C@@H:24]([F:27])[C@@H:23]3[C@H:19]2[CH2:20][NH:21][CH2:22]3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:34][N:35]([CH3:50])[CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH2:46][C:47](O)=[O:48].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[Cl:70]CCl>>[ClH:70].[CH3:50][N:35]([CH3:34])[CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH2:46][C:47]([N:21]1[CH2:20][C@@H:19]2[C@@H:23]([C@H:24]([F:27])[CH2:25][CH2:26][C:18]2([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:22]1)=[O:48]

Komponenten

7

Edukt 6

HCID 6344Dichloromethane2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9948096(3aR,7R,7aR)-4,4-diphenyl-7-fluoroperhydroisoindoleHCID 224172542-(3-Dimethylaminopropoxy)phenylacetic acid

Produkt 1

HCID 67809527(3aR,7R,7aR)-2-{[2-(3-dimethylaminopropoxy)phenyl]acetyl}-4,4-diphenyl-7-fluoroperhydroisoindole hydrochloride

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 0.5 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide in 50 cm3 of dry dichloromethane is added over 10 minutes to a solution, cooled to +4° C., of 0.72 g of (3aR,7R,7aR)-4,4-diphenyl-7-fluoroperhydroisoindole, 0.5 g of 2-(3-dimethylaminopropoxy)phenylacetic acid, 0.03 g of 1-hydroxybenzotriazole in 75 cm3 of dichloromethane, followed by 0.37 cm3 of diisopropylethylamine. The reaction mixture is stirred for 3 hours at 0° C. and then washed twice with 50 cm3 of water and twice with 50 cm3 of a saturated solution of sodium chloride. The organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 21 cm3 of 0.1N hydrochloric acid, 50 cm3 of diethyl ether and 30 cm3 of water. The aqueous phase is separated and freeze-dried to give 0.85 g of (3aR,7R,7aR)-2-{[2-(3-dimethylaminopropoxy)phenyl]acetyl}-4,4-diphenyl-7-fluoroperhydroisoindole hydrochloride, in the form of a white freeze-dried product.

Aufarbeitung

  1. washwashed twice with 50 cm3 of water and twice with 50 cm3 of a saturated solution of sodium chloride
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe aqueous phase is separated
  5. customfreeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-e13e5983a6474f6ba1ce1f91fac040c6
Quelldatensatz
uspto-grants-1995_09
Patentnummer
US05451601

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