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

HRID 1644241Notes

Reaction equation

HRID 1644241 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(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.

Workup

  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)

Sources & evidence

ORD record
ord-feb6951c34d641a1b5ac28d3cb18540e
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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