Triethylamine → n-Cbz-3-hydroxypiperidine

HRID 1654523Notes

Reaction equation

HRID 1654523 reaction equation
Cl.[OH:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C(N(CC)CC)C>O1CCOCC1.O>[CH2:13]([O:12][C:10]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([OH:2])[CH2:4]1)=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 2723962Piperidine-3-ol hydrochloride

Product 1

HCID 561665n-Cbz-3-hydroxypiperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-hydroxypiperidine hydrochloride (20.0 g, 0.145 mol) in dioxane (500 ml) and water (500 ml) was added benzyl chloroformate (24.88 ml, 0.17 mol) and triethylamine (101 ml, 0.73 mol). The mixture was stirred at room temperature overnight. The reaction mixture was extracted with ether and the organic layer was washed with brine, dried over magnesium sulfate and concentrated. The crude product was purified through chromatography on silica gel (eluent: 1:1 ethyl acetate/hexane) and the title compound was obtained as a pale yellow viscous oil (20.7 g, 88 mmol, yield 61%).

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified through chromatography on silica gel (eluent: 1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-aa10e06856c248c38fb5cc8394fffbd1
Source dataset
uspto-grants-1995_04
Patent number
US05407943

Reaction notes

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