Tert-butyl 3-oxopiperidine-1-carboxylate → 3-Methylene-piperidine-1-carboxylic acid tert-butyl ester

HRID 1771928Notes

Reaction equation

HRID 1771928 reaction equation
[I-].C1([C:8]([PH3+])([C:15]2[CH:20]=C[CH:18]=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(C)(C)C.[K+].[C:28]([N:35]1CCCC(=O)C1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>C1(C)C=CC=CC=1>[C:28]([N:35]1[CH2:18][CH2:17][CH2:16][C:15](=[CH2:20])[CH2:8]1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]

Participants

5

Reactant 3

HCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 23665647Potassium tert-butoxideHCID 66599960Tritylphosphanium iodide

Product 1

HCID 112525943-Methylene-piperidine-1-carboxylic acid tert-butyl esterYield 70.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of triphenylmethylphosphonium iodide (22.14 g) in toluene (135 ml) was added potassium tert-butanolate (5.32 g). The solution turned to orange. Then N-Boc-3-piperidone (6.0 g) in toluene (66 ml) was dropped into the solution under argon, at 30° C. The reaction was filtered and washed with water (200 ml, 2×) and then diluted by HCl (1M), dried with anhydrous sodium sulfate. The solution was purified by flash chromatography (silica gel, PE:EA=15:1) to obtain N-Boc-3-methylenepiperidine as an oil (4.2 g).

Workup

  1. filtrationThe reaction was filtered
  2. washwashed with water (200 ml, 2×)
  3. additiondiluted by HCl (1M)
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solution was purified by flash chromatography (silica gel, PE:EA=15:1)

Sources & evidence

ORD record
ord-deb06acb73144bdf93e284ffc0456ff9
Source dataset
uspto-grants-2016_02
Patent number
US09249154B2

Reaction notes

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