Ammonium Chloride → Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

HRID 47322Notes

Reaction equation

HRID 47322 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:15]([Mg]Br)[CH:16]=[CH2:17].[Cl-].[NH4+]>C(OCC)C>[CH2:17]([C:2]1([OH:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178455850HCID 178455850, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

800 ml solution of 25.0 g tert-butyl 4-oxo-1-piperidinecarboxylate in diethyl ether was cooled in ice/methanol, and 138 ml solution of allylmagnesium bromide (1 M in diethyl ether) was added dropwise thereinto. The reaction mixture was stirred for 3 hr and 10 min. The reaction solution was poured into a mixture of saturated aqueous ammonium chloride and ice. The diethyl ether layer was recovered and washed with brine. It was dried over anhydrous magnesium sulfate, and then filtered. The filtrate was evaporated, and the resulting residue was purified by silica gel column chromatography to give 15.9 g of tert-butyl 4-allyl-4-hydroxy-1-piperidinecarboxylate.

Workup

  1. customThe diethyl ether layer was recovered
  2. washwashed with brine
  3. dry with materialIt was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-11aed2d71e964a3bbac8429b05982f37
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Reaction notes

Loading…