Water → HCID 18423420, compound

HRID 1894944Notes

Reaction equation

HRID 1894944 reaction equation
[O:1]=[CH:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[CH3:17][Mg]Br.O>C1COCC1.C1(C)C=CC=CC=1.C1COCC1>[OH:1][CH:2]([CH3:17])[CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 962WaterHCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 18423420HCID 18423420, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

To a solution of 250 mg of tert-butyl 4-(2-oxoethyl)piperidine-1-carboxylate in 5 mL of THF was added 1.2 mL of 1.4M methyl magnesium bromide in toluene-THF, followed by stirring at room temperature for 2 hours. Water was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography [chloroform:methanol=1:0-10:1] to obtain 236 mg of tert-butyl 4-(2-hydroxypropyl)piperidine-1-carboxylate as a colorless oily substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [chloroform:methanol=1:0-10:1]

Sources & evidence

ORD record
ord-8facb2787e56480a9a23bb224ee81517
Source dataset
uspto-grants-2013_08
Patent number
US08513422B2

Reaction notes

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