Sodium borohydride → HCID 58554152、化合物

HRID 2410499ノート

反応式

HRID 2410499 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH3:15])=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH3:15])=[C:6]([CH2:7][OH:8])[CH:9]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 23091110HCID 23091110、化合物

生成物 1

HCID 58554152HCID 58554152、化合物収率 93.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 5-bromo-2-(2-methylpyrrolidin-1-yl)benzaldehyde (17 g, 63.4 mmol) in methanol (150 mL) under nitrogen was added sodium borohydride (2.41 g, 63.4 mmol) at 0° C. in portions. The reaction mixture was stirred at RT for 1 hour, then evaporated to remove methanol. The resulting crude was taken up with water (250 mL) and extracted with EtOAc (150 mL). The organic layer was washed with water, then dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a yellow oil (16 g, 93%). 1H NMR (DMSO-d6, 400 MHz) δ 7.53 (1H, d), 7.27 (1H, d), 6.87 (1H, d), 5.22 (1H, t), 4.42 (2H, m), 3.56 (1H, m), 3.36 (1H, m), 2.70 (1H, m), 2.49 (1H, m) 2.09 (1H, m), 1.83 (1H, m), 1.73 (1H, m), 1.47 (1H, m), 0.90 (3H, d).

後処理

  1. customevaporated
  2. customto remove methanol
  3. extractionextracted with EtOAc (150 mL)
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7ce135a72c65417a9e733cea75e668ee
出典データセット
uspto-grants-2014_08
特許番号
US08815919B2

反応ノート

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