Acetic Acid → tert-Butyl N-[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamate

HRID 446010Notes

Reaction equation

HRID 446010 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.C(O[BH-](O[C:25](=O)[CH3:26])OC(=O)C)(=O)C.[Na+].[C:29](O)(=O)[CH3:30].C(=O)(O)[O-].[Na+].O1C[CH2:41][CH2:40][CH2:39]1>O>[C:25]1([CH2:26][N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]2)[CH2:30][CH2:29][CH2:41][CH2:40][CH:39]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 71293652tert-Butyl N-[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamateYield 95.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of tert-butyl N-(piperidin-4-yl)carbamate (5.3 g, 26.5 mmol), 1-cyclohexane-1-carboxaldehyde (3.5 g, 31.8 mmol), sodium triacetoxyborohydride (7.29 g, 34.4 mmol), acetic acid (0.5 ml) and tetrahydrofuran (dehydrated) (80 ml) was stirred at room temperature for 85 hours and 30 minutes. Water and sodium bicarbonate were added to the reaction mixture, which was stirred and then extracted with ethyl acetate twice. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate/heptane) to give the title compound (7.47 g, yield: 95.7%).

Workup

  1. stirringwas stirred
  2. extractionextracted with ethyl acetate twice
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate/heptane)

Sources & evidence

ORD record
ord-61820cb1fdf84626b400f7cdbc6e4457
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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