2,6-Dichlorophenol → HCID 59177677, compound

HRID 1868083Notes

Reaction equation

HRID 1868083 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[Cl:46][C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[C:48]=1O>C1COCC1>[Cl:46][C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[C:48]=1[O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 68992,6-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 59177677HCID 59177677, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (3.7 g, 23 mmol) and triphenyl phosphine (12.23 g, 46 mmol) in 50 ml THF was mixed in an ice-H2O bath. A solution of diethyl azodicarboxylate (8.37 g, 46 mmol) in 50 ml THF was added drop-wise, followed by 2,6-dichlorophenol (3.87 g, 23 mmol). The mixture was warmed up to room temperature and stirred for 22 hr. Solvent was removed under vacuum and crude product was purified with column chromatography. tert-Butyl 4-(2,6-dichlorophenoxy)piperidine-1-carboxylate was obtained in 75% yield.

Workup

  1. customSolvent was removed under vacuum and crude product
  2. customwas purified with column chromatography

Sources & evidence

ORD record
ord-1c3a09ad83494fc5b4252e1ef01f1965
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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