Benzene, 1-bromo-3-nitro- → Tert-butyl 4-(2-bromo-4-nitrophenoxy)piperidine-1-carboxylate

HRID 1268198Notes

Reaction equation

HRID 1268198 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].[Br:15][C:16]1[CH:17]=[C:18]([N+:23]([O-:25])=[O:24])[CH:19]=[CH:20][C:21]=1O.BrC1C=C([N+]([O-])=O)C=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[Br:15][C:16]1[CH:17]=[C:18]([N+:23]([O-:25])=[O:24])[CH:19]=[CH:20][C:21]=1[O:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1

Participants

7

Reactant 5

HCID 11457Benzene, 1-bromo-3-nitro-HCID 11776TriphenylphosphineHCID 221092-Bromo-4-nitrophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 18542613Tert-butyl 4-(2-bromo-4-nitrophenoxy)piperidine-1-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (2.7 g), 3-bromo-4-hydroxynitrobenzene (1.9 g) [which was prepared from 3-bromonitrobenzene according to the method described in J. Org. Chem., 63 4199 (1998)] and triphenylphosphine (4.4 g) in dichloromethane (50 ml) was added dropwise diethyl azodicarboxylate (2.7 ml) and the mixture was stirred at room temperature for 11.5 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=2/1 as an eluant to give the desired compound (3.1 g, yield 91%) as a 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-8a0e5ffe410845ccb26f2caf3961a6f5
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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