Benzyl Alcohol → HCID 67000056, compound

HRID 560175Notes

Reaction equation

HRID 560175 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][C:18](N=[N+]=[N-])=[O:19])=[CH:12][C:11]([Br:23])=[CH:10][CH:9]=2)=[O:5])[CH3:2].S(O)(C1C=CC(C)=CC=1)(=O)=O.O.[CH2:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][C:18]([O:43][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:19])=[CH:12][C:11]([Br:23])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 58172051HCID 58172051, compound

Product 1

HCID 67000056HCID 67000056, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-(3-Azidocarbonyl-propyl)-5-bromo-1H-indole-2-carboxylic acid ethyl ester (1.28 g, 3.4 mmol, 1.0 equiv), TsOH hydrate (65 mg, 0.34 mmol, 0.1 equiv), and benzyl alcohol (0.74 mL, 6.8 mmol, 2.0 equiv) were refluxed in 30 mL of benzene for 16 h. The solution was then poured into saturated aqueous sodium bicarbonate (50 mL) and extracted with 2×50 mL of diethyl ether. The pooled organic fractions were dried (Na2SO4), filtered, and evaporated. The residue was purified by flash chromatography on silica gel using 0% EtOAc in hexanes graded to 20% EtOAc in hexanes to provide 5-bromo-3-[3-benzyloxycarbonyl-propyl]-1H-indole-2-carboxylic acid ethyl ester (1.3 g, 75%). This material was used without further manipulation.

Workup

  1. extractionextracted with 2×50 mL of diethyl ether
  2. dry with materialThe pooled organic fractions were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel using 0% EtOAc in hexanes

Sources & evidence

ORD record
ord-68704b4f231144c491cac0a4309c4157
Source dataset
uspto-grants-2011_11
Patent number
US08063094B2

Reaction notes

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