Dimethylformamide → tert-Butyl ethyl(piperidin-4-yl)carbamate

HRID 2301745Notes

Reaction equation

HRID 2301745 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[CH2:25](I)[CH3:26].CN(C=O)C.[H-].[Na+]>O>[C:21]([O:20][C:18]([N:17]([CH:14]1[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1)[CH2:25][CH3:26])=[O:19])([CH3:22])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 21981786Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

Product 1

HCID 18677728tert-Butyl ethyl(piperidin-4-yl)carbamateYield 126.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 476 mg (1.42 mmol) of 1-benzyloxycarbonyl-4-(t-butoxycarbonylamino)piperidine from Step B and 0.24 mL (2.8 mmol) of ethyl iodide in 10 mnL of DMF was added 85 mg (2.1 mmol) of 60% sodium hydride in mineral oil. The reaction was stirred for 16 h and was then poured into water and extracted three times with ether. The organic layers were each washed with a portion of water and brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FC eluting with 15% ethyl acetate in hexanes to afford 409 mg of title compound.

Workup

  1. extractionextracted three times with ether
  2. washeach washed with a portion of water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by FC
  6. washeluting with 15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-151a31d1bd584ba3b395ba561d8fcf23
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

Loading…