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

HRID 1924011노트

반응식

HRID 1924011 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a34209d9e5f54100aa7526a2c633288b
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178529B2

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