Sodium borohydride → HCID 11459077, compound

HRID 505356Notes

Reaction equation

HRID 505356 reaction equation
[CH2:1]1[O:17][C:16]2[CH:15]=[CH:14][C:5]([CH:6]=[N:7][CH2:8][CH:9]([O:12][CH3:13])[O:10][CH3:11])=[CH:4][C:3]=2[O:2]1.[BH4-].[Na+]>CO>[CH2:1]1[O:17][C:16]2[CH:15]=[CH:14][C:5]([CH2:6][NH:7][CH2:8][CH:9]([O:12][CH3:13])[O:10][CH3:11])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11149084(3,4-Methylenedioxybenzylidene)-(2,2-dimethoxyethyl)amine

Product 1

HCID 11459077HCID 11459077, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Imine 11b (10.74 g, 0.045 mol) was dissolved in methanol (100 mL) and NaBH4 (2×3 g) was added over 1 h while stirring the reaction mixture at room temperature. The reaction was quenched with methanol and the reaction mixture was concentrated and then diluted with diethyl ether (400 mL). The precipitate formed was removed by filtration. The filtrate was washed with water (2×200 mL), brine (200 mL), dried (Na2SO4) and concentrated to provide a yellow liquid (4.90 g, 46%). 1H NMR (300 MHz CDCl3) 6.79-6.69 (m, 3H), 5.86 (s, 2H), 4.41 (t, J=5.4 Hz, 1H), 3.64 (s, 2H), 3.30 (s, 6H), 2.65 (d, J=5.4 Hz, 2H).

Workup

  1. customThe reaction was quenched with methanol
  2. concentrationthe reaction mixture was concentrated
  3. additiondiluted with diethyl ether (400 mL)
  4. customThe precipitate formed
  5. customwas removed by filtration
  6. washThe filtrate was washed with water (2×200 mL), brine (200 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7cc22bd851464e53a38f6dfe0727dd42
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

Loading…