Water → HCID 20063333、化合物

HRID 1084457ノート

反応式

HRID 1084457 の反応式
[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

参加物

6

反応物 4

HCID 962Water2 回HCID 3283Diethyl EtherHCID 4148881Lithium borohydrideHCID 20063341HCID 20063341、化合物

生成物 1

HCID 20063333HCID 20063333、化合物収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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)].

後処理

  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)

出典と根拠

ORDレコード
ord-b756aca4fc714f16ac0a68b9d2d10e10
出典データセット
uspto-grants-1991_04
特許番号
US05004747

反応ノート

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