1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

HRID 1852717Notes

Reaction equation

HRID 1852717 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:9]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH:7]=[CH:6][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (312 g, 1.12 mol) and DBU (400 g, 2.24 mol) in THF (4.5 L) was heated to reflux overnight. The mixture was poured into ice-water (2 L) and then extracted with EtOAc (2 L). The combined organic phase was washed with 1 M HCl solution (4 L×2), aq. NaHCO3 (4 L), and dried over anhydrous sodium sulfate. The residue was concentrated to afford tert-butyl 3,6-dihydropyridine-1(2H)-carboxylate, which was used in the next step without further purification.

Workup

  1. temperatureto reflux overnight
  2. extractionextracted with EtOAc (2 L)
  3. washThe combined organic phase was washed with 1 M HCl solution (4 L×2), aq. NaHCO3 (4 L)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe residue was concentrated

Sources & evidence

ORD record
ord-c3c354e499d34a879921bcc86466b6fd
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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