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

HRID 1796209Notes

Reaction equation

HRID 1796209 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>ClCCl.N(C(OCC)=O)=NC(OCC)=O>[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]

Participants

6

Reactant 3

HCID 74422-Methyl-4-nitrophenolHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 220568ethyl N-ethoxycarbonyliminocarbamateSolvent

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), diethyl azodicarboxylate (3.2 ml) was added dropwise with stirring under ice-cooling, and the resulting mixture was stirred at room temperature overnight and then evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using dichloromethane as the eluent to afford the title compound (4.07 g) containing impurities as a pale yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. customevaporated in vacuo
  4. customThe residue obtained
  5. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-74ebbbe11e1a4d8e9e7c86414d916887
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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