(S)-Tert-butyl 4-methyl-4-(3-methylpiperazin-1-YL)piperidine-1-carboxylate → tert-Butyl 4-{(3S)-4-[(1R,2R)-5-Bromo-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-3-methylpiperazin-1-yl}-4-methylpiperidine-1-carboxylate

HRID 2244922Notes

Reaction equation

HRID 2244922 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[CH:7]3[O:8][CH:6]3[CH2:5][C:4]=2[CH:3]=1.[CH3:12][C:13]1([N:26]2[CH2:31][CH2:30][NH:29][C@@H:28]([CH3:32])[CH2:27]2)[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@@H:7]([N:29]1[CH2:30][CH2:31][N:26]([C:13]3([CH3:12])[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[CH2:27][C@@H:28]1[CH3:32])[C@H:6]([OH:8])[CH2:5]2

Participants

4

Reactant 2

HCID 17759466(S)-Tert-butyl 4-methyl-4-(3-methylpiperazin-1-YL)piperidine-1-carboxylateHCID 725319574-Bromo-6,6a-dihydro-1aH-indeno[1,2-b]oxirene

Product 1

HCID 68741279tert-Butyl 4-{(3S)-4-[(1R,2R)-5-Bromo-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-3-methylpiperazin-1-yl}-4-methylpiperidine-1-carboxylateYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-bromo-6,6a-dihydro-1aH-indeno[1,2-b]oxirene (247.9 mg, 1.1746 mmol) in ethanol (10.00 mL) was added tert-butyl 4-methyl-4-[(3S)-3-methylpiperazin-1-yl]piperidine-1-carboxylate (349.36 mg, 1.1746 mmol). The reaction mixture was heated to reflux overnight. After cooling down, the mixture was evaporated under reduced pressure. Purification on silica gel with 50% ethyl acetate (1% NH4OH) and hexane afforded the fast moving product as the desired compound (295 mg; 49.4%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling down
  4. customthe mixture was evaporated under reduced pressure
  5. customPurification on silica gel with 50% ethyl acetate (1% NH4OH) and hexane
  6. customafforded the

Sources & evidence

ORD record
ord-df7498de1e934a28a010a7515b02cc5b
Source dataset
uspto-grants-2010_03
Patent number
US07678798B2

Reaction notes

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