2,4-Dimethoxybenzaldehyde → Isohexane ethyl acetate

HRID 1183015Notes

Reaction equation

HRID 1183015 reaction equation
[NH2:1][CH:2]([CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@@H:16]2[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]2)=[CH:10][CH:9]=1)[C:3]#[N:4].[CH3:23][O:24][C:25]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:26]=1[CH:27]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:15][CH2:16][O:17][C:18]([CH3:21])=[O:19].[CH3:5][CH2:6][CH2:7][CH:8]([CH3:13])[CH3:9].[CH3:23][O:24][C:25]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:26]=1[CH2:27][NH:1][CH:2]([CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@@H:16]2[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]2)=[CH:10][CH:9]=1)[C:3]#[N:4]

Participants

7

Reactant 4

HCID 691752,4-DimethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 66917020HCID 66917020, compound2×

Product 2

HCID 21882781Isohexane ethyl acetateHCID 669170122-(2,4-Dimethoxy-benzylamino)-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-pentanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-amino-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-pentanenitrile (Intermediate B) (480 mg, 1.6 mmol) in DCM (13 mL) is added 2,4-dimethoxybenzaldehyde (319 mg, 1.92 mmol) and sodium triacetoxyborohydride (529 mg, 2.49 mmol) and the reaction is stirred at RT for 15 h. After this time saturated aqueous sodium hydrogen carbonate solution (20 mL) is added and the reaction is stirred at RT for 0.5 h. DCM (20 mL) is added and the layers are separated. The organic phase is washed with brine (20 mL) then dried over Na2SO4 and the solvent is removed in vacuo. Chromatography (SiO2, EtOAc:iso-hexane 2:3) affords the title compound as a colourless oil.

Workup

  1. stirringthe reaction is stirred at RT for 0.5 h
  2. customthe layers are separated
  3. washThe organic phase is washed with brine (20 mL)
  4. dry with materialthen dried over Na2SO4
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-2a04d8b7598b40238b7a8fc2ee51593d
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

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