Triethylamine → Benzyl 4-Hydroxy-1-piperidinecarboxylate

HRID 1291819Notes

Reaction equation

HRID 1291819 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[CH2:15]([O:22][C:23]([N:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

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

Product 1

HCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylateYield 63.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An ice-cooled solution containing 4-piperidinol (5 g, 50 mMoles) and triethylamine (7 ml, 50 mMoles) in dichloromethane (50 ml) was cautiously treated with benzylchloroformate (7.5 ml, 50 mMoles) and allowed to stir for 2 hours. Dichloromethane (25 ml) was added and the solution was washed sequentially with water (2×40 ml) and saturated brine (50 ml), then dried (MgSO4) and concentrated under reduced pressure. The residue was purified by vacuum flash chromatography, eluting with a gradient of 50-100% ether in hexane to give N-benzyloxycarbonyl piperidin-4-ol (7.5 g) as a colourless oil; NMR (d6DMSO): 1.2-1.4 (m,2H), 1.6-1.8 (m,2H), 3.0-3.2 (m,2H), 3.6-3.8 (m,3H), 4.7 (d,2H), 5.1 (2,2H), 7.3 (m,5H); m/e 236 (M+H)+.

Workup

  1. washthe solution was washed sequentially with water (2×40 ml) and saturated brine (50 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by vacuum flash chromatography
  5. washeluting with a gradient of 50-100% ether in hexane

Sources & evidence

ORD record
ord-109b1ae822d8481da6582117df32b6e7
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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