tert-butyl (2S)-2-methyl-4-oxopiperidine-1-carboxylate → (2S)-Tert-butyl 4-allyl-4-hydroxy-2-methylpiperidine-1-carboxylate

HRID 403506Notes

Reaction equation

HRID 403506 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][C@@H:9]1[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([Mg]Br)[CH:17]=[CH2:18]>CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][CH:17]=[CH2:16])([OH:14])[CH2:10][C@@H:9]1[CH3:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11401606tert-butyl (2S)-2-methyl-4-oxopiperidine-1-carboxylateHCID 178455850HCID 178455850, compound

Product 1

HCID 68379051(2S)-Tert-butyl 4-allyl-4-hydroxy-2-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

In a argon flushed dry 25 ml 2-neckoundbottomflask (S)-2-methyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (34) (0.6 g, 2.81 mmol) was dissolved in 10 ml of ether. A 1M solution of allylmagnesiumbromide in Et2O (3.66 ml, 3.66 mmol) was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 2 h. The mixture was quenched with NH4Cl solution and extracted with ether. The organic layer was washed with brine, dried over Na2 SO4 and evaporated. The crude product was purified by flash chromatography (silica gel, 20-30% EtOAc/cyclohexane) which furnished the product as white solid

Workup

  1. customIn a argon flushed
  2. customThe mixture was quenched with NH4Cl solution
  3. extractionextracted with ether
  4. washThe organic layer was washed with brine
  5. customdried over Na2 SO4
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (silica gel, 20-30% EtOAc/cyclohexane) which

Sources & evidence

ORD record
ord-821fde4c95414ddb8f3cf416e7d0b7fa
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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