Water → HCID 57095238, compound

HRID 439738Notes

Reaction equation

HRID 439738 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][C@H:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH2:9][NH:8][C:7]1=[O:21])=[O:5])[CH3:2].F[B-](F)(F)F.[CH3:27][O+](C)C.C(=O)([O-])[O-].[K+].[K+].O>C(Cl)(Cl)Cl>[CH3:27][O:21][C:7]1[CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][C@H:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH2:9][N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 11002702HCID 11002702, compound

Product 1

HCID 57095238HCID 57095238, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 515 mg of the product of Example 4 and 236 mg of trimethyloxonium tetrafluoroborate in 3 ml of chloroform was heated under reflux for four hours. The mixture was then cooled to ambient temperature, and 2 ml of 50% aqueous potassium carbonate was added. Then 10 ml of water and 10 ml of chloroform were added, and the organic phase, containing solids, was dried with magnesium sulfate. The solids were removed by filtration, and the supernatant was concentrated under vacuum. The residue was purified by spinning plate thin layer chromatography on a 2 mm silica gel plate, with 1:1 ethyl acetate:hexane, to obtain 286 mg of (3RS,5S)-2-methoxy-3-ethoxycarbonyl-5-[2-(4-bromophenyl)ethyl]-3,4,5,6-tetrahydropyridine, as a 1:1 mixture of the 3-position diastereomers.

Workup

  1. temperatureunder reflux for four hours
  2. additionthe organic phase, containing solids
  3. dry with materialwas dried with magnesium sulfate
  4. customThe solids were removed by filtration
  5. concentrationthe supernatant was concentrated under vacuum
  6. customThe residue was purified

Sources & evidence

ORD record
ord-6ec6f42e4ea0402fa64a570b7557c40b
Source dataset
uspto-grants-1996_05
Patent number
US05516776

Reaction notes

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