Triethylamine → Benzyl 4-Hydroxy-1-piperidinecarboxylate

HRID 1584373Notes

Reaction equation

HRID 1584373 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[OH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C>O1CCCC1>[OH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 79341Piperidin-4-ol

Product 1

HCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of benzyl chloroformate (35 ml, 247 mmol) in tetrahydrofuran (70 ml) was added to an ice-cold solution of 4-hydroxypiperidine (25 g, 247 mmol) and triethylamine (45 ml, 321 mmol) in tetrahydrofuran (350 ml). The mixture was stirred overnight at room temperature and the solvent removed under reduced pressure. The residue was partitioned between 5% hydrochloric acid and ethyl acetate, and the organic layer washed with brine, dried over magnesium sulfate, and the solvent removed under reduced pressure to give 4-hydroxy-N-CBZ-piperidine as a pale yellow oil.

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe residue was partitioned between 5% hydrochloric acid and ethyl acetate
  3. washthe organic layer washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-2d5ce28b25b843bdbbcb355200bd7d81
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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