Triethylamine → tert-Butyl 4-(ethylamino)piperidine-1-carboxylate

HRID 2301185Notes

Reaction equation

HRID 2301185 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:15]([N:17](CC)CC)[CH3:16].C([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CCO>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:17][CH2:15][CH3:16])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18374730tert-Butyl 4-(ethylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent2×

Procedure

To 5.0 g of N-Boc-4-piperidone were added 12.6 ml of titanium isopropoxide and 9.34 ml of triethylamine. This mixture was stirred for 1 hour, then 25 ml of EtOH (abs) and 1.056 g of sodium cyanoborohydride were added. The reaction was stirred for 48 hours at room temperature. EtOH and HsO were added and the reaction mixture was filtered through Celite. The solvent was then evaporated under reduced pressure. The residue was purified by flash chromatography with 10% EtOAc in hexane to give 3.548 g of the title compound.

Workup

  1. stirringThe reaction was stirred for 48 hours at room temperature
  2. filtrationthe reaction mixture was filtered through Celite
  3. customThe solvent was then evaporated under reduced pressure
  4. customThe residue was purified by flash chromatography with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-3510ee36a955467bad16fbe5ef893263
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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