Acetic Acid → 928649-00-7

HRID 1191012Notes

Reaction equation

HRID 1191012 reaction equation
C([BH3-])#N.[Na+].[C:5]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)#[N:6].[CH2:15]([NH2:19])[CH:16]([CH3:18])[CH3:17].C(O)(=O)C>CO>[CH2:15]([NH:19][CH2:11][C:10]1[CH:13]=[CH:14][C:7]([C:5]#[N:6])=[CH:8][CH:9]=1)[CH:16]([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6558IsobutylamineHCID 660424-CyanobenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 28428322928649-00-7Yield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere add sodium cyanoborohydride (5.77 g, 91.6 mmol) to 4-cyanobenzaldehyde (3 g, 22.9 mmol), iso-butylamine (3.34 g, 45.8 mmol) and acetic acid (1.37 g, 22.9 mmol) in methanol (30 mL) at 0° C. Warm the mixture to room temperature and stir overnight. Add water (40 mL), saturated aqueous K2CO3 (30 mL) and extract with DCM. Wash the combined organic extracts with water and brine. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel (500 g) eluting with 9:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the desired intermediate (3.63 g, 84%). MS (APCI+) m/z: 189 (M+H)+.

Workup

  1. extractionAdd water (40 mL), saturated aqueous K2CO3 (30 mL) and extract with DCM
  2. washWash the combined organic extracts with water and brine
  3. dry with materialDry the organic phase over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by chromatography on silica gel (500 g)
  7. washeluting with 9:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-918d97a1a9944926bd795e0452753c0b
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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