Water → {3-[4-(4-Azido-but-1-enyl)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-propyl}-carbamic acid tert-butyl ester

HRID 2036275노트

반응식

HRID 2036275 반응식
[Br-].[N:2]([CH2:5][CH2:6][CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[N+:3]=[N-:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:37]([O:41][C:42](=[O:60])[NH:43][CH2:44][CH2:45][CH2:46][O:47][C:48]1[C:57]2[CH2:56][CH2:55][CH2:54][CH2:53][C:52]=2[C:51]([CH:58]=O)=[CH:50][CH:49]=1)([CH3:40])([CH3:39])[CH3:38].O>C1COCC1>[C:37]([O:41][C:42](=[O:60])[NH:43][CH2:44][CH2:45][CH2:46][O:47][C:48]1[C:57]2[CH2:56][CH2:55][CH2:54][CH2:53][C:52]=2[C:51]([CH:58]=[CH:7][CH2:6][CH2:5][N:2]=[N+:3]=[N-:4])=[CH:50][CH:49]=1)([CH3:40])([CH3:39])[CH3:38]

참가 물질

6

반응물 4

HCID 962WaterHCID 2733832Lithium HexamethyldisilazideHCID 53362697(3-Azidopropyl)(triphenyl)phosphanium bromideHCID 57828234[3-(4-Formyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-propyl]-carbamic acid tert-butyl ester

생성물 1

HCID 76577162{3-[4-(4-Azido-but-1-enyl)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-propyl}-carbamic acid tert-butyl ester수율 48.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

(3-Azido-propyl)-triphenylphosphonium bromide (112, 11.5 g, 27 mmol) was stirred with 100 mL of dry THF at −76° C. LiHMDS (0.5 M in toluene, 27 mL) was added and the mixture was stirred for 30 minutes. [3-(4-Formyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-propyl]-carbamic acid tert-butyl ester (111, 6 g, 18 mmol) in 12 mL dry THF solution was introduced. The reaction mixture was stirred at this temperature for another 30 minutes, and slowly warmed to room temperature. The mixture was poured into water and extracted twice with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography (0-25% EtOAc/Hexane) to give 3.5 g 113 {3-[4-(4-azido-but-1-enyl)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-propyl}-carbamic acid tert-butyl ester.

후처리

  1. stirringThe reaction mixture was stirred at this temperature for another 30 minutes
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography (0-25% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-e39558b402874406a35474c51d396b19
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575176B2

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