Acetic Acid → HCID 18933005, compound

HRID 1598486Notes

Reaction equation

HRID 1598486 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([C:14]([O:16][CH3:17])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]1([CH:28]=O)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:28][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[CH:10]([C:14]([O:16][CH3:17])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 61951-NaphthaldehydeHCID 27568191-tert-Butyl 3-methyl piperazine-1,3-dicarboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18933005HCID 18933005, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Step B was dissolved in methanol (20 mL) with naphthalene-1-carboxaldehyde (0.67 mL, 4.7 mmol), sodium cyanoborohydride (0.350 g, 5.6 mmol) at pH 6 (adjusted with acetic acid) and the reaction stirred overnight. The solvent was evaporated and the residue partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate. The crude product was chromatographed on silica gel with ethyl acetate in hexane, and the title compound isolated as an oil. NMR (CDCl3, 300 MHz) d 8.34 (1H, d, J=7 Hz), 7.85 (1H, dm, J=7 Hz), 7.79 (1H, m), 7.51 (2H, m), 7.39 (2H, m), 4.34 (1H, d, J=12 Hz), 3.98 (1H, br s), 3.91 (1H, dd, J=12, 6 Hz), 3.75 (3H, s), 3.60 (1H, br s), 3.44 (1H, d, J=12 Hz), 3.27 (1H, t, J=3 Hz), 3.19 (1H, d, J=12 Hz), 3.09 (1H, td, J=10, 3 Hz), 2.42 (1H, br s), 1.44 (9H, s).

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product was chromatographed on silica gel with ethyl acetate in hexane

Sources & evidence

ORD record
ord-f295393efb9d4801acb0619c84893d4b
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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