Triethylamine → Benzyl 4-Hydroxy-1-piperidinecarboxylate

HRID 977014Notes

Reaction equation

HRID 977014 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>ClCCl>[CH2:19]([O:18][C:16]([N:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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 6344DichloromethaneSolvent2×

Procedure

A solution containing 4-piperidinol (5 g) and triethylamine (7 ml) in dichloromethane (50 ml) was treated with benzyl chloroformate (7.5 ml), added dropwise, and the resulting mixture was allowed to stand for 2 hours. The mixture was diluted with dichloromethane (50 ml) and washed with water (2×50 ml) and with saturated brine (50 ml). The organic solution was dried (MgSO4) and concentrated. The residue was purified by column chromatography, eluting with ether/hexane (50%, then 75%) followed by ether, to give 1-(benzyloxycarbonyl)piperidin-4-ol (7.5 g) as a colourless oil; NMR Spectrum 1.2-1.4 (2H, m); 1.6-1.8 (2H, m); 3.0-3.2 (2H, m); 3.6-3.8 (3H, m); 4.7 (1H, d); 5.05 (2H, s); 7.3-7.4 (5H, m).

Workup

  1. additionadded dropwise
  2. washwashed with water (2×50 ml) and with saturated brine (50 ml)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with ether/hexane (50%

Sources & evidence

ORD record
ord-8b72548d948544f5b8b8f32abc4dac3c
Source dataset
uspto-grants-1997_03
Patent number
US05612373

Reaction notes

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