Water → Benzyl 4-Hydroxy-1-piperidinecarboxylate

HRID 1381487Notes

Reaction equation

HRID 1381487 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].O>C(Cl)Cl>[CH2:21]([O:20][C:18]([N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 79341Piperidin-4-olHCID 81531Diisopropylethylamine

Product 1

HCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Hydroxypiperidine (10 g., 0.099 mole) and N,N-diisopropylethylamine (87 ml., 0.495 mole) were dissolved in methylene dichloride (200 ml.). The solution was cooled (ice bath) and protected from atmospheric moisture (drying tube), and benzyl chloroformate (14.1 ml., 16.9 g., 0.099 mole) was added over 2 hrs. Water (20 ml.) was added and the solvents were evaporated in vacuo (approx. 1 mm. pressure, solid CO2 cold finger condenser). The residue was shaken together with water (200 ml.) and ethyl acetate (200 ml.), and the mixture was separated. The organic phase was washed with water (4×50 ml.), dried (Na2SO4), and the solvent evaporated to give 1-benzyloxycarbonyl-4-hydroxypiperidine as a colourless oil, I.R.λmax 3800 cm.-1 and 1685 cm.-1.

Workup

  1. temperatureThe solution was cooled (ice bath)
  2. additionwas added over 2 hrs
  3. customthe solvents were evaporated in vacuo (approx. 1 mm. pressure, solid CO2 cold finger condenser)
  4. customthe mixture was separated
  5. washThe organic phase was washed with water (4×50 ml.)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-0d2da652e290467ba8c7c14cf818c8dc
Source dataset
uspto-grants-1989_02
Patent number
US04803201

Reaction notes

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