Triphenylphosphine → 4-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3,5-difluoronitrobenzene

HRID 1268222Notes

Reaction equation

HRID 1268222 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].[F:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[C:18]([F:25])[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[C:18]([F:25])=[CH:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][C:16]=2[F:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6002102,6-Difluoro-4-nitrophenolHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 185427114-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3,5-difluoronitrobenzeneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (1.73 g), 2,6-difluoro-4-nitrophenol (1.37 g) and triphenylphosphine (2.67 g) in dichloromethane (30 ml) was added dropwise diethyl azodicarboxylate (1.57 ml) in an ice bath and the mixture was stirred at room temperature for 9 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=6/1 as an eluant to give the desired compound (2.13 g, yield 76%) as a pale yellow 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-819ee1a67d5248c58ffd6849c1c5ef6d
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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