Sodium borohydride → HCID 11196128, compound

HRID 505362Notes

Reaction equation

HRID 505362 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:4]=1[CH:5]=[N:6][CH2:7][CH:8]([O:11][CH3:12])[O:9][CH3:10].[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:4]=1[CH2:5][NH:6][CH2:7][CH:8]([O:9][CH3:10])[O:11][CH3:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11436703HCID 11436703, compound

Product 1

HCID 11196128HCID 11196128, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Amine 11d (10.64 g, 0.042 mol) was dissolved in ethanol (100 mL) and NaBH4 (2.6 g) was added and the reaction mixture was stirred at 80-90° C. After 3 h the TLC indicated the absence of the starting material. The organic layer was washed with water (2×200 mL), brine (200 mL), dried (Na2SO4) and concentrated to provide a colorless oil (10.71 g, 100%). 1H NMR (300 MHz CDCl3) 6.79-6.67 (m, 3H), 4.43 (t, J=5.7 Hz, 1H), 3.72 (s, 3H), 3.71 (s, 3H), 3.68 (d, J=2.7 Hz, 2H), 3.28 (s, 6H), 2.7 (s, 2H).

Workup

  1. washThe organic layer was washed with water (2×200 mL), brine (200 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-31dac3da37244ef58aa0f07de7c5e845
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

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