Ethyl Acetate → methyl(R)-2-tert-butoxycarbonylamino-6-oxo-6-(3,4,5-trifluorophenyl)hexanoate

HRID 1436120Notes

Reaction equation

HRID 1436120 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4].[F:19][C:20]1[CH:21]=[C:22]([Mg]Br)[CH:23]=[C:24]([F:27])[C:25]=1[F:26].[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[C:15]([O:14][C:12]([NH:6][C@H:5]([CH2:10][CH2:9][CH2:8][C:7](=[O:11])[C:22]1[CH:21]=[C:20]([F:19])[C:25]([F:26])=[C:24]([F:27])[CH:23]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 107298291-(Tert-butyl) 2-methyl (R)-6-oxopiperidine-1,2-dicarboxylateHCID 178505944HCID 178505944, compound

Product 1

HCID 69005362methyl(R)-2-tert-butoxycarbonylamino-6-oxo-6-(3,4,5-trifluorophenyl)hexanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-6-oxopiperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (CAS No. 183890-36-0, 7.5 g) in THF (200 mL), 3,4,5-trifluorophenylmagnesium bromide (0.35 M solution in diethyl ether, 100 mL) was added dropwise at −40° C., and the reaction solution was stirred at room temperature for six hours. A saturated ammonium chloride solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1) to obtain 4.0 g of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3daec054f30b46bbad7d06d645bf4bb1
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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