Tert-butyl 4-hydroxypiperidine-1-carboxylate → HCID 67512170, compound

HRID 2404430Notes

Reaction equation

HRID 2404430 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5](=[N+]=[N-])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>ClCCCl>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:14])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 534012722-Diazonio-1-ethoxy-2-phenylethen-1-olate

Product 1

HCID 67512170HCID 67512170, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of diazophenylacetic acid ethyl ester (2.55 g) in 1,2-dichloroethane is added 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (5.4 g). The flask is evacuated and filled with argon. Rhodium(II) acetate-dimer (60 mg) is added to the reaction mixture. Evolution of nitrogen occurs until the end of the reaction (about 1 hour). The solvent is removed under reduced pressure. The residue is purified by chromatography (gradient heptane/ethyl acetate from 95/5 to 80/20) to give 4-(ethoxy-carbonylphenylmethoxy)piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe flask is evacuated
  2. additionfilled with argon
  3. additionRhodium(II) acetate-dimer (60 mg) is added to the reaction mixture
  4. customEvolution of nitrogen occurs until the end of the reaction (about 1 hour)
  5. customThe solvent is removed under reduced pressure
  6. customThe residue is purified by chromatography (gradient heptane/ethyl acetate from 95/5 to 80/20)

Sources & evidence

ORD record
ord-0e8f04a1fdd64cb589d719f59fb45563
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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