Acetic Acid → HCID 59807125, compound

HRID 1922455Notes

Reaction equation

HRID 1922455 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)[CH2:6][CH2:5]2.C=O.[C:18](O)(=O)C.[BH3-]C#N.[Na+].[OH-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:15][CH2:14][N:13]([CH3:18])[CH2:12]1)[CH2:6][CH2:5]2

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 59807071HCID 59807071, compound

Product 1

HCID 59807125HCID 59807125, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 2 (1.0 g, 3.743 mmol) in dry methanol (10 mL) was treated with HCHO (0.36 g, 4.491 mmol, 37% in water) followed by acetic acid (0.53 mL, 9.357 mmol) and NaCNBH3 (0.28 g, 4.491 mmol) at room temperature and the resulting mixture was stirred for over night (14 h). The reaction was basified with 2 N NaOH solution (50 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined organic layer was washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in methanol:CH2Cl2, 5:95) to obtain compound 3 (0.7 g, 66.6%) as a syrup. 1H NMR (CDCl3) δ 7.12-7.08 (m, 2H), 6.35 (d, 1H, J=9.0 Hz), 4.19-4.10 (m, 1H), 3.45-3.39 (m, 2H), 2.91 (t, 2H, J=8.1 Hz), 2.70-2.63 (m, 3H), 2.51-2.43 (m, 1H), 2.34 (s, 3H), 2.19-2.07 (m, 1H), 1.93-1.81 (m, 1H); ESI-MS (m/z, %): 281, 283 (MH+, 100).

Workup

  1. extractionwas extracted into CH2Cl2 (2×25 mL)
  2. washThe combined organic layer was washed with brine (15 mL)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was evaporated
  5. customcrude was purified by column chromatography (2 M NH3 in methanol:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-61787e589b4e48409984b33edef508e0
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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