HCID 54062527, compound → HCID 22128508, compound

HRID 1858578Notes

Reaction equation

HRID 1858578 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][O:12][CH:13]3[CH:18]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][O:12][CH:13]3[CH:18]([C:19]4[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=4)[CH2:17][CH2:16][NH:15][CH2:14]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 54062527HCID 54062527, compound

Product 1

HCID 22128508HCID 22128508, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 280 mg (0.63 mmol) of tert-butyl (3RS,4RS)-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethoxy)-4-(4-fluorophenyl)-piperidine-1-carboxylate in 5 ml of dry methylene chloride was treated with 808 mg (1.89 mmol) of anhydrous zinc bromide and the mixture was stirred at room temperature for 5 hours. Subsequently, the solvent was distilled off under reduced pressure, the residue was taken up in 10 ml of methanol, treated with 2 ml of 2N sodium hydroxide solution and the solid was separated. The filtrate was evaporated under reduced pressure and the residue was partitioned between methylene chloride and water. The organic phase was separated and evaporated under reduced pressure. There were obtained 220 mg (98% of theory) of (3RS,4RS)-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl-methoxy)-4-(4-fluorophenyl)-piperidine as a yellowish solid; MS: 344 (M+H)+.

Workup

  1. distillationSubsequently, the solvent was distilled off under reduced pressure
  2. additiontreated with 2 ml of 2N sodium hydroxide solution
  3. customthe solid was separated
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe residue was partitioned between methylene chloride and water
  6. customThe organic phase was separated
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a041aa7b316e4b2a8c6499e5878704f9
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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