1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69160387, compound

HRID 1392702Notes

Reaction equation

HRID 1392702 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@H:9]2[C:11](N2C=CN=C2)=[O:12])=[CH:4][CH:3]=1.[CH3:18][C@@H:19]1[C@H:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:22][C:21](=[O:30])[NH:20]1.C1CCN2C(=NCCC2)CC1>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:10][CH:9]2[C:11]([N:20]2[C@@H:19]([CH3:18])[C@@H:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:22][C:21]2=[O:30])=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2733812(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinoneHCID 69158073HCID 69158073, compound

Product 1

HCID 69160387HCID 69160387, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (cis)-1-{[2-(4-bromophenyl)cyclopropyl]carbonyl}-1H-imidazole (1 eq) from Step 1, (4R,5S)-(+)-4-methyl-5-phenyl-2-oxazolidinone (1.2 eq) or (−)-isomer and DBU (added at 0° C., 1.2 eq) in CH3CN (0.2M) was stirred at 0° C. for 4 h. The solvent evaporated and residue purified by flash chromatography (Hexane:EtOAc; 100:0 to 80:20) to afford each diastereoisomer.

Workup

  1. customThe solvent evaporated
  2. customresidue purified by flash chromatography (Hexane:EtOAc; 100:0 to 80:20)
  3. customto afford each diastereoisomer

Sources & evidence

ORD record
ord-04e5bc3fb4f844108aa1a774ab191767
Source dataset
uspto-grants-2008_03
Patent number
US07342024B2

Reaction notes

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