3,4-Dichlorophenol → HCID 22322443, compound

HRID 1292753Notes

Reaction equation

HRID 1292753 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:32][C:33]1[CH:34]=[C:35]([OH:40])[CH:36]=[CH:37][C:38]=1[Cl:39].O[CH:42]1[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]1>O1CCCC1>[Cl:32][C:33]1[CH:34]=[C:35]([CH:36]=[CH:37][C:38]=1[Cl:39])[O:40][CH:42]1[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]1

Participants

6

Reactant 4

HCID 72583,4-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22322443HCID 22322443, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl azodicarboxylate (41 ml) was added to a solution of triphenylphosphine (62.9 g) in tetrahydrofuran (800 ml) at 0° C. After 15 minutes 3,4-dichlorophenol (39.1 g) was added, after a further 15 minutes tert-butyl 4-hydroxy-1-piperidinecarboxylate (48.3 g) in tetrahydrofuran (400 ml) was added dropwise over 30 minutes. The solution was stirred at room temperature for 16 hours and concentrated to a small volume. Purification by flash chromatography (silica) eluting with ethyl acetate: iso-hexane (95:5) gave the sub-title compound as an oil (61.3 g).

Workup

  1. additionwas added dropwise over 30 minutes
  2. concentrationconcentrated to a small volume
  3. customPurification by flash chromatography (silica)
  4. washeluting with ethyl acetate: iso-hexane (95:5)

Sources & evidence

ORD record
ord-3df3b0892bd142a3aff76e283da9b433
Source dataset
uspto-grants-2007_07
Patent number
US07238691B2

Reaction notes

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