Borane → HCID 15516069, compound

HRID 1936601Notes

Reaction equation

HRID 1936601 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([CH:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1)=O)(=[O:12])=[O:11])([O-])=O.B>O1CCCC1>[CH2:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:31][CH2:32][CH:23]1[CH2:21][NH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:1])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 6331BoraneHCID 22462213HCID 22462213, compound

Product 1

HCID 15516069HCID 15516069, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2,3,4-tetrahydro-2-naphthalencarboxylic acid[6-(2-nitrobenzenesulfonylamino)-hexyl]- amide (0.090 g, 0.19 mmol) in tetrahydrofuran(5 mL) cooled to 0° C. was added 2 mL 1M solution of borane:THF complex and the reaction mixture was refluxed for 12 h. The reaction mixture was cooled in an ice bath and quenched with 2 mL of 1N HCl. The reaction mixture was neutralized with 10% aqueous sodium hydroxide solution and extracted with ethyl acetate (3×25 mL). The organic phase was washed with brine, dried over sodium sulfate, and evaporated in vacuo to afford an oil which was purified by preparative TLC to afford the titled compound(0.06 g, 70%); hydrochloride salt mp (162-163° C.).

Workup

  1. temperatureTHF complex and the reaction mixture was refluxed for 12 h
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. customquenched with 2 mL of 1N HCl
  4. extractionextracted with ethyl acetate (3×25 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customto afford an oil which
  9. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-f24d1205ce3e4c61a844ffd44ed86be7
Source dataset
uspto-grants-2002_05
Patent number
US06391877B1

Reaction notes

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