Hydrochloric Acid → HCID 68813721, compound

HRID 2103344Notes

Reaction equation

HRID 2103344 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([O:20][CH2:21][C:22]([NH:24][CH3:25])=O)[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.[ClH:27]>C1COCC1>[ClH:27].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([O:20][CH2:21][CH2:22][NH:24][CH3:25])[CH2:15][CH2:14][CH2:13]3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 57804252HCID 57804252, compound

Product 1

HCID 68813721HCID 68813721, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-N-methyl-acetamide (0.7 g, 1.9 mmol) was dissolved in 25 mL of dry THF. Borane (10 mL of 1N THF solution) was added, and the reaction mixture was refluxed for three hours under nitrogen. The reaction mixture was cooled and 25 mL of 25% aqueous HCl was added. The reaction mixture was refluxed for 10 minutes, cooled, and solvent was removed under reduced pressure. The aqueous residue was basified by dropwise addition of 1N aqueous NaOH, and the aqueous mix was extracted three times with 50 mL of EtOAc. The combined organic layers were washed with water, brine, and dried over MgSO4. The residue was recrystallized from Et2O/MeOH/HCl to give 380 mg (1.1 mmol, 58%) of [2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-ethyl]-methyl-amine hydrochloride. MS: 346 (M+H)+.

Workup

  1. temperaturethe reaction mixture was refluxed for three hours under nitrogen
  2. temperatureThe reaction mixture was cooled
  3. temperatureThe reaction mixture was refluxed for 10 minutes
  4. temperaturecooled
  5. customsolvent was removed under reduced pressure
  6. additionThe aqueous residue was basified by dropwise addition of 1N aqueous NaOH
  7. additionthe aqueous mix
  8. extractionwas extracted three times with 50 mL of EtOAc
  9. washThe combined organic layers were washed with water, brine
  10. dry with materialdried over MgSO4
  11. customThe residue was recrystallized from Et2O/MeOH/HCl

Sources & evidence

ORD record
ord-cc923dee20fb4467a5d7de28289b22d3
Source dataset
uspto-grants-2009_08
Patent number
US07576103B2

Reaction notes

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