Sodium cyanoborohydride → 3-Phenyl-2-furanmethanamine

HRID 915689

Reaction equation

HRID 915689 reaction equation
[C:1]1([C:7]2[CH:11]=[CH:10][O:9][C:8]=2[CH:12]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH3-]C#[N:16].[Na+]>CO>[C:1]1([C:7]2[CH:11]=[CH:10][O:9][C:8]=2[CH2:12][NH2:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 134657043-Phenylfuran-2-carbaldehyde

Product 1

HCID 691299233-Phenyl-2-furanmethanamineYield 13.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir a solution of 3-phenylfuran-2-carbaldehyde (401 mg, 2.33 mmol) and NH4OAc (1.79 g, 23.30 mmol) in methanol (8 mL) at room temperature under nitrogen. Add NaCNBH3 (102 mg, 1.63 mmol). After stirring at room temperature for 24 hours, concentrate the mixture, dilute with water (2 mL), basify with 1N sodium hydroxide, and extract with diethyl ether (4×10 mL). Dry the combined organic phases (magnesium sulfate), filter and concentrate. Perform flash chromatography on silica gel eluting with 9:1 ethyl acetate/MeOH to afford 37 mg of the title compound as a yellow solid. 1H NMR (CDCl3) δ 7.19-7.41 (m, 6H), 6.49 (d, J=2 Hz, 1H), 3.95(s, 2H), 1.80 (br s, 2H).

Workup

  1. concentrationconcentrate the mixture
  2. additiondilute with water (2 mL), basify with 1N sodium hydroxide
  3. extractionextract with diethyl ether (4×10 mL)
  4. dry with materialDry the combined organic phases (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-04b5727dfaa54c1e9c06cb272af8238e
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Linked notes

Loading…