Sodium Hydroxide → HCID 86598340, Verbindung

HRID 1270417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270417
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[C:6]([N:8]1[C@H:13]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:12][N:11]2[CH2:24][C:25](=[O:28])[CH2:26][CH2:27][C@@H:10]2[CH2:9]1)=[O:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:4]=[C:5]([C:6]([N:8]2[C@H:13]([CH2:14][C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][CH:16]=3)[CH2:12][N:11]3[CH2:24][C@@H:25]([OH:28])[CH2:26][CH2:27][C@@H:10]3[CH2:9]2)=[O:7])[CH:29]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:31]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 18449067HCID 18449067, Verbindung

Produkt 1

HCID 86598340HCID 86598340, VerbindungAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of (3R,9aR)-2-[3,5-bis(trifluoromethyl)benzoyl]-3-(1H-indol-3-ylmethyl)-octahydro-2H-pyrido[1,2-a]pyrazin-7-one (5.6 g) in acetic acid (75 mL) was added sodium triacetoxyborohydride (6.78 g). The resulting mixture was stirred for one hour at room temperature then poured in water and basified with 2M sodium hydroxide (aq.). The formed precipitate was collected by filtration, washed with water, suspended in toluene and concentrated in vacuo to afford 3,5-bis(trifluoromethyl) phenyl-[(3R,7S,9aR)-7-hydroxy-3-(1H-indol-3-ylmethyl)-octahydropyrido[1,2-a]pyrazin-2-yl]-methanone (5.7 g). Rf 0.35 (CH2Cl2/MeOH 9:1) (compound 12).

Aufarbeitung

  1. filtrationThe formed precipitate was collected by filtration
  2. washwashed with water
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6d24e17890d947ddb4919619b3e76b90
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202238B2

Notizen zur Reaktion

Wird geladen…