1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-tert-Butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate

HRID 1987517Notes

Reaction equation

HRID 1987517 reaction equation
CS(O[CH:6]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8][CH:7]1[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=O)=O.C1CCN2C(=NCCC2)CC1>C1C=CC=CC=1>[N:10]1([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:11][CH2:12][CH:6]=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 87134947HCID 87134947, compound

Product 1

HCID 251945651-tert-Butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylateYield 95.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of example 42C (0.77 g, 2.1 mmol) in 30 mL of benzene was treated with DBU (0.9 ml ) at 60° C. for 1 hour. After cooling, the reaction mixture was concentrated and the residue was purified by flash column chromatography (30% EtOAc in hexane) to give the title product (540 mg, 95% yield). MS (DCI/NH3) m/z 270 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by flash column chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-06095512b15b4060bc5f862c8735b3d9
Source dataset
uspto-grants-2009_06
Patent number
US07550603B2

Reaction notes

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