Toluene → HCID 18538752, compound

HRID 412922Notes

Reaction equation

HRID 412922 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1.[OH:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.[CH3:34][S:35][C:36]1[CH:41]=[CH:40][C:39](O)=[CH:38][CH:37]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.C1COCC1>[CH3:34][S:35][C:36]1[CH:41]=[CH:40][C:39]([O:20][CH:21]2[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]2)=[CH:38][CH:37]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 140864-(Methylthio)phenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 18538752HCID 18538752, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of diethyl azodicarboxylate in toluene (6.76 ml, 14.9 mmol) was added dropwise to a mixture of tert-butyl 4-hydroxypiperidine-1-carboxylate (2 g, 9.94 mmol), 4-(Methylsulfanyl)phenol (2,8 g, 20 mmol), triphenylphosphine (3.9 g, 15 mmol) and THF (20 ml) over the period of 0.5 h at 0° C. The resulting solution was stirred at room temperature for 3 d. The mixture was diluted in ethyl acetate (20 ml) and the whole was washed with 1N aqueous sodium hydroxide (20 ml), 0.5N hydrochloric acid (20 ml) and saturated sodium chloride solution (20 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel 25 g, ethyl acetate/hexane=1/20 to 1/10) to give the title compound (1.8 g, 52%) as a colorless powder.

Workup

  1. washthe whole was washed with 1N aqueous sodium hydroxide (20 ml), 0.5N hydrochloric acid (20 ml) and saturated sodium chloride solution (20 ml)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography (silica gel 25 g, ethyl acetate/hexane=1/20 to 1/10)

Sources & evidence

ORD record
ord-e83e5a949e1544ee8adcd92eaf7c7278
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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