Water → HCID 22128780, compound

HRID 1858655Notes

Reaction equation

HRID 1858655 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][C:29]3([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[O:33][CH2:32][CH2:31][O:30]3)=[CH:21][CH:20]=2)[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1.O>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][C:29]3([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[O:33][CH2:32][CH2:31][O:30]3)=[CH:21][CH:20]=2)[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

5

Reactant 2

HCID 962WaterHCID 54060942HCID 54060942, compound

Product 1

HCID 22128780HCID 22128780, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 600 mg (0.962 mmol) of tert-butyl (3RS,4RS)-3-(naphthalen-2-ylmethoxy)-4-{4-[3-(2-phenyl-[1,3]dioxolan-2-yl)-propoxy]-phenyl}-piperidine-1-carboxylate in 3.0 ml of methylene chloride and 433 mg (1.92 mmol, 2.0 eq.) of zinc bromide was stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted three times with ethyl acetate. The organic phases were washed in each case once with water and with saturated sodium chloride solution, dried over magnesium sulphate, evaporated under reduced pressure and dried in a high vacuum. The amorphous, slightly yellow crude product was separated on silica gel using a 95:5:0.1 mixture of methylene chloride, methanol and ammonia. There were obtained 355 mg (71% of theory) of (3RS,4RS)-3-(naphthalen-2-ylmethoxy)-4-[4-[3-(2-phenyl-[1,3]dioxolan-2-yl)-propoxy]-phenyl]-piperidine as a colourless resin; MS: 524 (M+H)+.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe organic phases were washed in each case once with water and with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customdried in a high vacuum
  6. customThe amorphous, slightly yellow crude product was separated on silica gel using
  7. additiona 95:5:0.1 mixture of methylene chloride, methanol and ammonia

Sources & evidence

ORD record
ord-ad8ce163d17f45d0bd504203e81df70e
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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