Triphenylphosphine → HCID 67348329, compound

HRID 1672839Notes

Reaction equation

HRID 1672839 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19](O)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([O:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 122723-IodophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 67348329HCID 67348329, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3-Iodophenol (1.00 g, 4.55 mmol) and 1-tert-butoxycarbonyl-4-hydroxypiperidine (1.37 g, 6.82 mmol) were dissolved in toluene (30 mL), and the mixture was stirred at room temperature for 1 hour after adding triphenylphosphine (1.79 g, 6.82 mmol) and a 40% toluene solution of diethyl azodicarboxylate (3.09 mL, 6.82 mmol). The mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 1-tert-butoxycarbonyl-4-(3-iodophenoxy)piperidine (1.81 g, 98%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff645a33656b46c7a16670a96f83d2ee
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

Loading…