Acetic Acid → tert-Butyl 4-[4-(1H-tetrazol-1-yl)anilino]-1-piperidinecarboxylate

HRID 412900Notes

Reaction equation

HRID 412900 reaction equation
[N:1]1([C:6]2[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1>[N:1]1([C:6]2[CH:12]=[CH:11][C:9]([NH:10][CH:23]3[CH2:24][CH2:25][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:21][CH2:22]3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5716404-(1H-1,2,3,4-tetrazol-1-yl)anilineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 18539221tert-Butyl 4-[4-(1H-tetrazol-1-yl)anilino]-1-piperidinecarboxylateYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1H-tetrazol-1-yl)aniline (2 g, 12.4 mmol) and 1-tert-butoxycarbonyl-4-piperidone (3.71 g, 18.6 mmol) in THF (15 ml) were added acetic acid (1.42 ml, 24.8 mmol) and sodium triacetoxyborohydride (4 g, 18.6 mmol), successively, under ice cooling, and the mixture was stirred for 20 hours. To the mixture was added sodium triacetoxyborohydride (4 g, 18.6 mmol), and the mixture was stirred at room temperature for 20 hours. To the mixture was added saturated aqueous solution of sodium hydrogencarbonate (100 ml), and the mixture was stirred at room temperature for 1 hour. The mixture was extracted with ethyl acetate (100 ml), and the organic layer was washed with saturated sodium chloride solution (50 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the concentrate was added diisopropyl ether (20 ml), and the resulting precipitates were collected by filtration to give the titled compound (4.2 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionThe mixture was extracted with ethyl acetate (100 ml)
  4. washthe organic layer was washed with saturated sodium chloride solution (50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the concentrate was added diisopropyl ether (20 ml)
  8. customthe resulting precipitates
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-cd2ed117637349a7baee0934ce2df531
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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