Triphenylphosphine → HCID 18542820, compound

HRID 1043796Notes

Reaction equation

HRID 1043796 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[OH:32][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.[CH3:46][O:47][C:48]1[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:49]=1O>C1COCC1>[CH3:46][O:47][C:48]1[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:49]=1[O:32][CH:33]1[CH2:34][CH2:35][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:37][CH2:38]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 767382-Methoxy-4-nitrophenolHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 18542820HCID 18542820, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture under N2 of triphenylphosphine (3.10 g, 11.825 mmol) and diethylazodicarboxylate (2.06 g, 11.825 mmol) in THF (40 mL) was added tert-butyl 4-hydroxypiperidine-1-carboxylate (2.00 g, 9.937 mmol). After stirring 10 min, 2-methoxy-4-nitrophenol (1.00 g, 5.912 mmol) was added. The reaction stirred 16 h and evaporated under reduced pressure to give an orange oil. The crude product was purified by column chromatography on silica gel using 25% EtOAc/hexane yielding tert-butyl 4-(2-methoxy-4-nitrophenoxy)piperidine-1-carboxylate as a beige solid (1.70 g, 82%). LC/MS (m/z): 3512 (MH+), Rt 3.23 minutes

Workup

  1. stirringThe reaction stirred 16 h
  2. customevaporated under reduced pressure
  3. customto give an orange oil
  4. customThe crude product was purified by column chromatography on silica gel using 25% EtOAc/hexane

Sources & evidence

ORD record
ord-1344384d2b1049c7ae0d32c8fcca3c6b
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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