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

HRID 73174ノート

反応式

HRID 73174 の反応式
[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]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15227139HCID 15227139、化合物

生成物 1

HCID 597523872-Azido-4-methyl-cyclohexanecarboxylic acid ethyl ester収率 65%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1371b19076594710a9c43fcf45b0476c
出典データセット
uspto-grants-2014_09
特許番号
US08829030B2

反応ノート

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