Triphenylphosphine → Tert-butyl 4-((6-chloropyridin-3-yl)oxy)piperidine-1-carboxylate

HRID 1467964Notes

Reaction equation

HRID 1467964 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](O)=[CH:18][N:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:15][C:16]1[N:17]=[CH:18][C:19]([O:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 8198212-Chloro-5-hydroxypyridineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 86696180Tert-butyl 4-((6-chloropyridin-3-yl)oxy)piperidine-1-carboxylateYield 45.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (15.5 g, 77 mmol), 2-Chloro-5-hydroxy-pyridine (9.9 g, 77 mmol) and triphenylphosphine (24.24 g, 92.4 mmol) in THF, diisopropylazodicarboxylate (18.6 g, 92.4 mmol) was added at 0° C. and stirred for 18 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo, resulting residue was purified by flash column chromatography to give tert-butyl 4-((6-chloropyridin-3-yl)oxy)piperidine-1-carboxylate (11 g, 45%); MS: 335.2 (M+23).

Workup

  1. additionwas added at 0° C.
  2. customThe reaction was quenched with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. concentrationThe organic layer was concentrated in vacuo
  5. customresulting residue
  6. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-f5b76466c52c41e49265f682042edbfb
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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