1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 23368628, compound

HRID 1901805Notes

Reaction equation

HRID 1901805 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:35])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1)(=[O:24])=[O:23])[CH2:17][C:18]([O:20][CH3:21])=[O:19].C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[Cl:15][C:13]1[CH:14]=[C:9]2[C:10](=[CH:11][CH:12]=1)[N:16]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1)(=[O:23])=[O:24])[CH:17]([C:18]([O:20][CH3:21])=[O:19])[C:8]2([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[OH:35]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23368633HCID 23368633, compound

Product 1

HCID 23368628HCID 23368628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.3 g of the compound obtained in step B are dissolved at 0° C. in 13 ml of DCM in the presence of 180 mg of DBU. After stirring overnight, the reaction medium is poured directly on to a silica column prepared in DCM and the mixture of compounds resulting from cyclization is thus separated by elution with DCM. Chromatography is then carried out on alumina using a DCM/isopropyl ether mixture (70/30, v/v) as the eluent. The cis isomer is thus isolated.

Workup

  1. additionthe reaction medium is poured directly on to a silica column
  2. additionthe mixture of compounds
  3. customresulting from cyclization
  4. customis thus separated by elution with DCM
  5. customThe cis isomer is thus isolated

Sources & evidence

ORD record
ord-7e3a87bfb6f940c0ba92c9c0a32c96e2
Source dataset
uspto-grants-1996_11
Patent number
US05578633

Reaction notes

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