Triethylamine → 1-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

HRID 2365174Notes

Reaction equation

HRID 2365174 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:17](OC([O-])=O)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>C(#N)C>[C:20]([O:19][C:17]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 739534-PiperidineethanolHCID 22064466Tert-butyldicarbonate

Product 1

HCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-piperidine ethanol (1.95 g) in acetonitrile (25 mL) was added triethylamine (2.53 mL) followed by tert-butyl dicarbonate (3.63 g). The mixture was stirred at room temperature for 22 hours and partitioned between 0.5 M hydrochloric acid and ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and the solvent evaporated to give 4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (3.46 g).

Workup

  1. custompartitioned between 0.5 M hydrochloric acid and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-316e71d09a234e43b18c24cf64799a2c
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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