Triphenylphosphine → 4-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3-isopropylnitrobenzene

HRID 1268201Notes

Reaction equation

HRID 1268201 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].[CH:15]([C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1O)([CH3:17])[CH3:16].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:19]2[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:18]=2[CH:15]([CH3:17])[CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5289542-Isopropyl-4-nitrophenolHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 185426424-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3-isopropylnitrobenzeneYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (2.96 g), 2-isopropyl-4-nitrophenol (2.66 g) and triphenylphosphine (5.00 g) in dichloromethane (80 ml) was added diethyl azodicarboxylate (3.0 ml) and the mixture was stirred at room temperature for 2 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 desired compound (4.07 g, yield 76%) as a brown solid.

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-d96f0cceb9c44baf9ef062013db16a04
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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