Triethylamine → tert-Butyl 2-oxopiperidine-1-carboxylate

HRID 1054439Notes

Reaction equation

HRID 1054439 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:7].C(N(CC)CC)C.[O:15](C(OC(C)(C)C)=O)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=O>C(#N)C.CN(C1C=CN=CC=1)C>[O:7]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][N:1]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 126652-PiperidoneHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateYield 63.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of piperidin-2-one (25 g, 252.2 mmol) in acetonitrile (250 ml) was cooled to 0° C. and added DMAP (6.1 g, 50.4 mmol) and triethyl amine (25.5 g, 252.2 mmol) and stirred for 10 min at same temperature then added (BOC)2O (66 g, 302.6 mmol) and continue stirring for 2 h at room temperature. After completion of starting material, solvent was removed and residue was re-dissolved in ethyl acetate and washed with water, brine and dried over Na2SO4 and concentration to afford crude product as brown liquid (31.8 g) which was used directly for the next step. 1H NMR (300 MHz, CDCl3) δ 3.66-3.62 (2H, m), 2.52-2.47 (2H, m), 1.83-1.79 (4H, m), 1.52 (9H, s) ppm.

Workup

  1. customAfter completion of starting material, solvent was removed
  2. dissolutionresidue was re-dissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4 and concentration

Sources & evidence

ORD record
ord-ff64d5bb1ea34e8ca575e7fbbfec25fb
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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