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

HRID 1635662Notes

Reaction equation

HRID 1635662 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 mins. 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-6bcf47333ff34cbf9b1f4f50a2a24175
Source dataset
uspto-grants-2003_01
Patent number
US06509464B1

Reaction notes

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