Water → Tert-butyl 1-[2-(benzyloxy)-2-oxoethyl]piperidine-4-carboxylate

HRID 1469141Notes

Reaction equation

HRID 1469141 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.Br[CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].O>C(#N)C>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][N:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][CH2:2]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62576Benzyl bromoacetateHCID 81531DiisopropylethylamineHCID 1512676Tert-butyl Piperidine-4-carboxylate

Product 1

HCID 66588152Tert-butyl 1-[2-(benzyloxy)-2-oxoethyl]piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension (39 mL) of tert-butyl piperidine-4-carboxylate (2.6 g) in acetonitrile was added diisopropylethylamine (4.4 mL), subsequently, benzyl bromoacetate (2.0 mL) was added at room temperature in portions, and the mixture was stirred for 4 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. This was washed with an aqueous saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:3→0:1) to obtain the title compound (3.4 g) having the following physical property values.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThis was washed with an aqueous saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:3→0:1)

Sources & evidence

ORD record
ord-4ed0a03ca2c54bd1b30750e4acf982e5
Source dataset
uspto-grants-2015_04
Patent number
US09006246B2

Reaction notes

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