2,4,4,6-Tetrabromocyclohexa-2,5-dienone → methyl (2S)-1-(6-bromo-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate

HRID 841937Notes

Reaction equation

HRID 841937 reaction equation
Br[C:2]1[C:3](=O)[C:4](Br)=[CH:5][C:6]([Br:9])(Br)[CH:7]=1.[O:12]1C2C=CC=CC=2[N:14]=[C:13]1[N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[C:27]([O:29][CH3:30])=[O:28]>ClCCl>[Br:9][C:6]1[CH:7]=[CH:2][C:3]2[N:14]=[C:13]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]3[C:27]([O:29][CH3:30])=[O:28])[O:12][C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienoneHCID 10220819methyl (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylate

Product 1

HCID 9949771methyl (2S)-1-(6-bromo-1,3-benzoxazol-2-yl)-2-piperidinecarboxylateYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one (4.7 g) was added to a solution of methyl (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylate (3.0 g) [see Preparation 2] in dichloromethane (60 ml) at −10° C. over a period of 10 minutes. The reaction mixture was then warmed to room temperature and diluted with dichloromethane. The organic layer was washed with saturated sodium hydrogen carbonate, then with 1N sodium hydroxide solution, dried over sodium sulphate and the solvent removed under reduced pressure to afford methyl (2S)-1-(6-bromo-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate (3.7 g) as a purple coloured oil.

Workup

  1. washThe organic layer was washed with saturated sodium hydrogen carbonate
  2. dry with materialwith 1N sodium hydroxide solution, dried over sodium sulphate
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-db20bcff907d43f8b1d43f0c373c1717
Source dataset
uspto-grants-2002_04
Patent number
US06372736B1

Reaction notes

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