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

HRID 1694407

反応式

HRID 1694407 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 672792521-(3,5-Difluorobenzyl)pyrrolidine収率 74%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-2090fbbe074e4ccebf96bc4aa6be1629
出典データセット
uspto-grants-2012_04
特許番号
US08158673B2

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