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2-Methyl-4-nitrophenol → tert-Butyl 4-(2-methyl-4-nitrophenoxy)piperidine-1-carboxylate

HRID 1268185
Notes
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Reaction equation

HRID 1268185 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].[CH3:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:17]2[CH:18]=[CH:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][C:16]=2[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 74422-Methyl-4-nitrophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22181075tert-Butyl 4-(2-methyl-4-nitrophenoxy)piperidine-1-carboxylateYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (3.62 g), 2-methyl-4-nitrophenol (2.55 g) and triphenylphosphine (5.25 g) in dichloromethane (100 ml) was added dropwise diethyl azodicarboxylate (3.2 ml) in an ice bath and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane as an eluant to give the crude desired compound (4.07 g) as a pale yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-dcb99d196976440bb313d93cc85e56c1
Source dataset
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06555556B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes