Acetic Acid → Sodium Bicarbonate

HRID 1827286Notes

Reaction equation

HRID 1827286 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10]1([N:16]2[C:20]3([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[C:19](=[O:26])[NH:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:27]([OH:30])(=[O:29])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+:44]>C1COCC1.O>[C:27](=[O:29])([OH:9])[O-:30].[Na+:44].[Br:1][C:2]1[C:7]([CH2:8][N:23]2[CH2:22][CH2:21][C:20]3([N:16]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH2:17][NH:18][C:19]3=[O:26])[CH2:25][CH2:24]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 47149512-BromonicotinaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 516892Sodium BicarbonateHCID 22136241HCID 22136241, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-bromo-pyridine-3-carbaldehyde (0.68 g, 3.6 mmol) were added 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (0.846 g, 3.6 mmol), and acetic acid (1.1 g, 18 mmol) in THF (40.0 ml) and sodium triacetoxyborohydride (1.55 g, 7.3 mmol) and the resulting reaction mixture stirred at room temperature overnight. Water (50 ml) was added and the reaction mixture solution was extracted with ethyl acetate three times. The combined organic layers were dried over MgSO4. The solvent was removed and the resulting residue was purified over silica gel column eluted with methylene chloride (97%), methanol (2%), acetic acid (1%) and then with saturated sodium bicarbonate solution to yield 8-(2-bromo-pyridin-3-ylmethyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one as a white solid.

Workup

  1. customthe resulting reaction mixture
  2. extractionthe reaction mixture solution was extracted with ethyl acetate three times
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customThe solvent was removed
  5. customthe resulting residue was purified over silica gel column
  6. washeluted with methylene chloride (97%), methanol (2%), acetic acid (1%)

Sources & evidence

ORD record
ord-a24144b80e424a62913afa19b3c73302
Source dataset
uspto-grants-2006_05
Patent number
US07053101B2

Reaction notes

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