1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 58237935, compound

HRID 1192928Notes

Reaction equation

HRID 1192928 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:11][CH2:12][CH2:13][C:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH2:21][CH:22]=[CH2:23])[CH2:15][C:16]([O:18]CC)=O)[CH2:9][CH3:10])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[CH2:21]([C:14]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:13][CH2:12][N:11]([C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH2:9][CH3:10])[C:16](=[O:18])[CH2:15]1)[CH:22]=[CH2:23]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58237944HCID 58237944, compound

Product 1

HCID 58237935HCID 58237935, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 3-(2-((S)-1-(4-bromophenyl)propylamino)ethyl)-3-phenylhex-5-enoate (0.5028 g, 1.10 mmol) and DBU (1.30 g, 8.54 mmol) in toluene (10 mL) was heated to reflux under nitrogen for 2 d. The reaction mixture was cooled to rt, quenched with 2 N aq HCl, extracted with EtOAc, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford 0.3045 g (67%) of 4-allyl-1-((S)-1-(4-bromophenyl)propyl)-4-phenylpiperidin-2-one. LC-MS Method 3 tR=2.18, 2.22 min, m/z 412, 414 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 2 d
  3. customquenched with 2 N aq HCl
  4. extractionextracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. customAfter the solvents were evaporated
  7. customthe residue was purified by chromatography on silica gel
  8. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-3afc6b1c08794f528f167d98a836a81f
Source dataset
uspto-grants-2014_03
Patent number
US08680281B2

Reaction notes

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