4-Bromo-3-fluorobenzaldehyde → (3S,5S)-4-(4-bromo-3-fluorobenzyl)-3,5-dimethylmorpholine

HRID 1924011ノート

反応式

HRID 1924011 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[F:10].[CH3:11][C@H:12]1[CH2:17][O:16][CH2:15][C@H:14]([CH3:18])[NH:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:13]2[C@@H:14]([CH3:18])[CH2:15][O:16][CH2:17][C@@H:12]2[CH3:11])=[CH:4][C:3]=1[F:10]

参加物

5

反応物 3

HCID 27834114-Bromo-3-fluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11768549(3S,5S)-3,5-Dimethylmorpholine

生成物 1

HCID 59543856(3S,5S)-4-(4-bromo-3-fluorobenzyl)-3,5-dimethylmorpholine収率 30.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

4-Bromo-3-fluorobenzaldehyde (0.250 g, 1.23 mmol) and (3S,5S)-3,5-dimethylmorpholine (0.205 g, 1.35 mmol) were dissolved in dichloromethane (10 mL). Sodium triacetoxyborohydride (0.378 g, 1.79 mmol) was added and the mixture was stirred under argon atmosphere at RT for 20 h. The mixture was diluted with dichloromethane and washed with NaHCO3 (aq). The organic phase was dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica eluting with gradients of ammonia in methanol and dichloromethane. The fractions containing product were pooled and evaporated to give (3S,5S)-4-(4-bromo-3-fluorobenzyl)-3,5-dimethylmorpholine (0.113 g, 30%) as a liquid.

後処理

  1. washwashed with NaHCO3 (aq)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica eluting with gradients of ammonia in methanol and dichloromethane
  5. additionThe fractions containing product
  6. customevaporated

出典と根拠

ORDレコード
ord-a34209d9e5f54100aa7526a2c633288b
出典データセット
uspto-grants-2012_05
特許番号
US08178529B2

反応ノート

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