Sodium borohydride → 6-Hydroxymethyl-3-(3-methylisoxazol-5-yl)-4-phenyl-1H-quinolin-2-one

HRID 2053430

反応式

HRID 2053430 の反応式
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:25])[NH:9][C:10]3[C:15]([C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:13]([CH:23]=[O:24])=[CH:12][CH:11]=3)[O:4][N:3]=1.[BH4-].[Na+]>C(Cl)Cl.CO>[OH:24][CH2:23][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:25])[C:7]([C:5]1[O:4][N:3]=[C:2]([CH3:1])[CH:6]=1)=[C:16]2[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 1360186723-(3-Methyl-isoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxaldehyde

生成物 1

HCID 1354058036-Hydroxymethyl-3-(3-methylisoxazol-5-yl)-4-phenyl-1H-quinolin-2-one収率 90.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-(3-methyl-isoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydro-quinoline-6-carboxaldehyde (a) (33 mg, 0.11 mmol), sodium borohydride (NaBH4) (4 mg, 0.1 mmol) in DCM (1 mL) and methanol (1 mL) was stirred at room temperature for 1.5 h, and then concentrated. To the residue was added DCM (10 mL) and water (1 mL). The organic layer was separated from the aqueous layer, dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel to give 6-hydroxymethyl-3-(3-methylisoxazol-5-yl)-4-phenyl-1H-quinolin-2-one (c) (33 mg, 90%). 1H NMR (300 MHz, CD3OD) δ 7.65-7.58 (m, 1H), 7.49-7.38 (m, 4H), 7.30-7.20 (m, 3H), 6.30 (s, 1H), 4.51 (s, 2H), 2.17 (s, 3H). MS: 333.2 (M+H).

後処理

  1. concentrationconcentrated
  2. additionTo the residue was added DCM (10 mL) and water (1 mL)
  3. customThe organic layer was separated from the aqueous layer
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-08e9e172fc454ade96f72a1ebdf97d1b
出典データセット
uspto-grants-2008_02
特許番号
US07326788B2

関連ノート

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