Triphenylphosphine → HCID 15392246, compound

HRID 1700292Notes

Reaction equation

HRID 1700292 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:33]1[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:42]([O:41][C:39]([N:36]1[CH2:37][CH2:38][CH:33]([O:1][C:2]2[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=2)[CH2:34][CH2:35]1)=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 819940methyl 2-amino-5-hydroxybenzoateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 15392246HCID 15392246, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-hydroxy-2-(methoxycarbonyl)benzenamine (6.8 g), triphenylphosphine (14.2 g) and 4-hydroxy-N-(t-butoxycarbonyl)piperidine (9.06 g) in THF (200 mL) was added DEAD (9.51 g) drop-wise at ambient temperature. The reaction was stirred at ambient temperature for overnight, concentrated and re-dissolved in ether. The ether layer was washed with 0.5 N NaOH aqueous solution, water and brine. It was then concentrated and purified on silica gel column (ethyl acetate/hexane, gradient) to afford 4-(N′-(t-butoxycarbonyl)piperidin-4-yl)oxy-2-(methoxycarbonyl)benzenamine (7.31 g).

Workup

  1. concentrationconcentrated
  2. dissolutionre-dissolved in ether
  3. washThe ether layer was washed with 0.5 N NaOH aqueous solution, water and brine
  4. concentrationIt was then concentrated
  5. custompurified on silica gel column (ethyl acetate/hexane, gradient)

Sources & evidence

ORD record
ord-01875675a2d94d3ca74d5aae116a1554
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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