Triphenylphosphine → HCID 24883361, compound

HRID 2103322Notes

Reaction equation

HRID 2103322 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:15][C:16]1[CH:29]=[CH:28][C:19]([O:20][C:21]2[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=2)=[CH:18][CH: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[CH:29]=[CH:28][C:19]([O:20][C:21]2[CH:26]=[CH:25][C:24]([O:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:23][CH:22]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 123461204-(4-Chlorophenoxy)phenol

Product 1

HCID 24883361HCID 24883361, compoundYield 153.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of t-butyl-4-hydroxy-1-piperidinecarboxylate (0.40 g, 1.99 mmol) in anhydrous THF (8 mL) was added 4-(4-chloro-phenoxy)-phenol (0.58 g, 2.61 mmol) and triphenylphosphine (0.63 g, 2.40 mmol). The resulting mixture was cooled to 0° C. Diisopropylazodicarboxylate (0.47 mL, 2.43 mmol) was added portionwise over a ten minute period. The reaction mixture was warmed to ambient temperature for an hour and then heated to 47° C. for 64 h. The solvent was removed in vacuo. The crude residue was purified by silica gel flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.93 g, 100%) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was warmed to ambient temperature for an hour
  2. temperatureheated to 47° C. for 64 h
  3. customThe solvent was removed in vacuo
  4. customThe crude residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-5660a56923854c99a173675cc10e5bc5
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

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