1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine → tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

HRID 1670625Notes

Reaction equation

HRID 1670625 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1CCN2C(=NCCC2)CC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[CH:11][CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneSolvent

Procedure

Heat a solution of 4-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (0.69 mol, 193 g) in DBU (400 mL) at 80° C. for 16 h. Dilute the reaction mixture with water, extract with diethyl ether, and wash the organic layer with 1 N hydrochloric acid and saturated sodium bicarbonate solution. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound (116 g, 92%) as a brown oil. 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 2.12 (br s, 2H), 3.47 (t, 2H), 3.87 (s, 2H), 5.65 (br s, 1H), 5.81 (br s, 1H).

Workup

  1. extractionextract with diethyl ether
  2. washwash the organic layer with 1 N hydrochloric acid and saturated sodium bicarbonate solution
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-9b90d854c4304df782a3be7dc48fa0e8
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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