Pyrrolidine → 1-(3,5-Difluorobenzyl)pyrrolidine

HRID 1694407

반응식

HRID 1694407 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

참가 물질

7

반응물 4

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 5881603,5-DifluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 672792521-(3,5-Difluorobenzyl)pyrrolidine수율 74%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

3,5-Difluorobenzaldehyde (2.0 mL, 18.24 mmol), pyrrolidine (1.8 mL, 21.56 mmol), and sodium triacetoxyborohydride (5.8 g, 27.4 mmol) were stirred in THF (50 mL) for 16 h at room temperature. Saturated aqueous NaHCO3 (30 mL) was added and after stirring for 30 min, EtOAc (50 mL) was added. The organic phase was separated and washed with brine, dried over MgSO4 and concentrated to afford 2.65 g (74%) of 1-(3,5-difluorobenzyl)pyrrolidine as a slightly cloudy oil: 1H NMR (CDCl3) δ 6.88-6.83 (m, 1H), 6.68-6.63 (m, 2H), 3.59 (s, 2H), 2.53-2.48 (m, 4H), 1.80-1.77 (m, 4H).

후처리

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2090fbbe074e4ccebf96bc4aa6be1629
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158673B2

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