Water → HCID 20063333, Verbindung

HRID 1084457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1084457
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]([C:18](Cl)=[O:19])=[C:16]([CH:21]([CH3:23])[CH3:22])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:24])=[CH:4][CH:3]=1.[BH4-].[Li+].O.C(OCC)C>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]([CH2:18][OH:19])=[C:16]([CH:21]([CH3:22])[CH3:23])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:24])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 3283Diethyl EtherHCID 4148881Lithium borohydrideHCID 20063341HCID 20063341, Verbindung

Produkt 1

HCID 20063333HCID 20063333, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A stirred solution of crude 2-(4-fluorophenyl)-4-isopropyl-1-oxo-1,2-dihydroisoquinoline-3-carbonyl chloride (21 g) in dry tetrahydrofuran (300 ml) was treated dropwise with a solution of lithium borohydride in tetrahydrofuran (26 ml; 2.0M) and the mixture stirred at room temperature for 18 hours. The reaction mixture was then treated dropwise with water (50 ml), diethyl ether (500 ml) and more water (200 ml) and the organic layer was separated, washed with water (200 ml) and brine (200 ml), dried over magnesium sulphate and evaporated to leave a yellow oil. This was triturated with a hot mixture of diethyl ether (200 ml) and n-hexane (400 ml) to give 2-(4-fluorophenyl)-3-hydroxymethyl-4-isopropyl-1-oxo-1,2-dihydroisoquinoline (13.7 g) in the form of a white solid, m.p. 157°-158° C. [Elemental analysis: C, 73.1; H, 5.7; N, 4.4%; calculated: C, 73.3; H, 5.8; N, 4.5%; NMR (in CDCl3): 1.55 (7H, d, J=8 Hz,), 3.65 (1H, sept, J=8 Hz), 4.4 (2H, s), 7.1-7.4 (4H, m), 7.5 (1H, t, J=8 Hz,), 7.7 (1H, t, J=8 Hz), 8.04 (1H, d, J=8 Hz), 8.5 (1H, d, J=8 Hz)].

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with water (200 ml) and brine (200 ml)
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customto leave a yellow oil
  6. customThis was triturated with a hot mixture of diethyl ether (200 ml) and n-hexane (400 ml)

Quellen und Nachweise

ORD-Eintrag
ord-b756aca4fc714f16ac0a68b9d2d10e10
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05004747

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