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Phenol → TERT-BUTYL 4-PHENOXYPIPERIDINE-1-CARBOXYLATE

HRID 1585242
Notes
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Reaction equation

HRID 1585242 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15]1(O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 12063835TERT-BUTYL 4-PHENOXYPIPERIDINE-1-CARBOXYLATEYield 66%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 403 mg (2.0 mmol) of N-tert-butoxycarbonyl-4-hydroxypiperidine, 188 mg (2.0 mmol) of phenol, and 525 mg (2.0 mmol) of triphenylphosphine in 50 mL of THF was added 0.315 mL of diethylazodicarboxylate. The resulting solution was stirred at room temperature for 2 days. Concentration in vacuo and purification via silica gel chromatography (10:1 hexane-EtOAc) provided 366 mg of the title compound as a colorless oil.

Workup

  1. concentrationConcentration
  2. customin vacuo and purification via silica gel chromatography (10:1 hexane-EtOAc)

Sources & evidence

ORD record
ord-b689391e5e8c40859830d7fc914995f5
Source dataset
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05936089

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes