HCID 86604431, compound → HCID 22127548, compound

HRID 1005082Notes

Reaction equation

HRID 1005082 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:13]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH:9]2[CH:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[CH:4][CH:3]=1>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:13]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)[CH2:12][NH:11][CH2:10][CH:9]2[CH:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86604431HCID 86604431, compound

Product 1

HCID 22127548HCID 22127548, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

40 mg (0.08 mmol) of tert-butyl (3SR,4RS,5RS)-4-(4-chloro-phenyl)-3-(1-ethyl-propyl)-5-(naphthalen-2-ylmethoxy)-piperidine-carboxylate were dissolved in 5 ml of dry methylene chloride and treated with 35 mg (0.16 mmol) of anhydrous zinc bromide in an analogous manner to the procedure described by A. Mann et al. in Synth. Comm. 19(18), 3139-3142 (1989). The reaction mixture was stirred at room temperature for 5 hours. For the working-up, the reaction mixture was evaporated under reduced pressure and the crude product obtained was purified by chromatography on silica gel using a 90:10:0.1 mixture of methylene chloride, methanol and ammonia as the eluent. There were obtained 28 mg (86% of theory) of (3SR,4RS,5RS)-4-(4-chloro-phenyl)-3-(1-ethyl-propyl)-5-(naphthalen-2-ylmethoxy)-piperidine as a colourless oil; MS: 422 (M+H)+.

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customthe crude product obtained
  3. customwas purified by chromatography on silica gel using
  4. additiona 90:10:0.1 mixture of methylene chloride, methanol and ammonia as the eluent

Sources & evidence

ORD record
ord-eeece24dab0e4897a822a7817e9102a0
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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