Triphenylphosphine → 2-Azido-4-methyl-cyclohexanecarboxylic acid ethyl ester

HRID 73174Notes

Reaction equation

HRID 73174 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8][CH:7]1O)=[O:5])[CH3:2].C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8][CH:7]1[N:28]=[N+:29]=[N-:30])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15227139HCID 15227139, compound

Product 1

HCID 597523872-Azido-4-methyl-cyclohexanecarboxylic acid ethyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Hydroxy-4-methyl-cyclohexanecarboxylic acid ethyl ester (495 mg, 2.66 mmol) was dissolved in THF (13 ml) and then diphenylphosphoryl azide (680 ul, 3.19 mmol) and triphenylphosphine (837 mg, 3.19 mmol) were added. The resulting solution was cooled in an ice bath and diethyl azodicarboxylate (502 ul, 3.19 mmol) was added. After stirring at room temperature for 20 hours, the solvents were removed and the residue was purified by flash chromatography (0% to 3% EtOAc/Hexane) to obtain 365 mg (65%) of 2-Azido-4-methyl-cyclohexanecarboxylic acid ethyl ester.

Workup

  1. temperatureThe resulting solution was cooled in an ice bath
  2. customthe solvents were removed
  3. customthe residue was purified by flash chromatography (0% to 3% EtOAc/Hexane)

Sources & evidence

ORD record
ord-1371b19076594710a9c43fcf45b0476c
Source dataset
uspto-grants-2014_09
Patent number
US08829030B2

Reaction notes

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