tert-Butyl 4-oxopiperidine-1-carboxylate → Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

HRID 1059329Notes

Reaction equation

HRID 1059329 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15]([Mg]Br)[CH:16]=[CH2:17].P([O-])(O)(O)=O.[Na+]>C(OCC)C>[CH2:17]([C:11]1([OH:14])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]1)[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 23672064Monosodium phosphateHCID 178455850HCID 178455850, compound

Product 1

HCID 21955339Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Into a solution of 4.98 g of 1-(tert-butoxycarbonyl)-4-piperidone in diethyl ether (150 ml) was dropped at 0° C. in a nitrogen atmosphere 30 ml of a 1.0 M solution of allylmagnesium bromide in diethyl ether and the resulting mixture was stirred for 3 hours. Then the reaction mixture was poured into an aqueous solution of sodium dihydrogenphosphate and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 4.12 g of the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7ecb15cdb12d4dde8e01ab87ce848fcd
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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