Hexane → 1-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate

HRID 1773315Notes

Reaction equation

HRID 1773315 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].CCN(CC)CC.[O:20](C(OC(C)(C)C)=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=O.CCCCCC>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])[CH2:4][CH:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 1073164-Oxo-piperidine-3-carboxylic acid ethyl ester

Product 1

HCID 64208761-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylateYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-oxopiperidine-3-carboxylate (180.0 g, 0.87 mol, 1.0 eq.) in DCM (2.7 L) was added Et3N (352.14 g, 3.48 mol, 4.0 eq.) dropwise at 15° C. and stirred for 30 min followed by addition of (BOC)2O (210.0 g, 0.96 mol, 1.10 eq.) maintaining the temperature below 10° C. The resulted mixture was stirred at rt overnight, and concentrated to give a crude product that was stirred with hexane (3.5 L) for 1 h and filtered. The filtered cake was washed with hexanes. The combined organic phase was concentrated to furnish the title compound (226.0 g, 0.83 mol, 95.4%).

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. stirringThe resulted mixture was stirred at rt overnight
  3. concentrationconcentrated
  4. customto give a crude product that
  5. filtrationfiltered
  6. washThe filtered cake was washed with hexanes
  7. concentrationThe combined organic phase was concentrated

Sources & evidence

ORD record
ord-7ca7a6158f554644964c681c9531b5f6
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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