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

HRID 73174노트

반응식

HRID 73174 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1371b19076594710a9c43fcf45b0476c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829030B2

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