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

HRID 1943270Notes

Reaction equation

HRID 1943270 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-25505d1f39fb4b058ff584721ce1637e
Source dataset
uspto-grants-2013_03
Patent number
US08389743B2

Reaction notes

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