Hydrochloric Acid → HCID 86626019, compound

HRID 870365Notes

Reaction equation

HRID 870365 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:26][C@@H:25]4[C@H:20]([CH2:21][CH2:22][CH2:23][N:24]4[C:27](=O)[CH2:28][CH3:29])[CH2:19][C:18]=3[CH:31]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].B.O1CCCC1.Cl>O1CCCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:26][C@@H:25]4[C@H:20]([CH2:21][CH2:22][CH2:23][N:24]4[CH2:27][CH2:28][CH3:29])[CH2:19][C:18]=3[CH:31]=2)(=[O:12])=[O:11])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 86626017HCID 86626017, compound

Product 1

HCID 86626019HCID 86626019, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.18 mg of trans-4-isopropyl-N-(1-propionyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-7-yl)-benzenesulfonamide (0.268 mmol) were dissolved in 7 ml of tetrahydrofuran. 1.4 ml of 1 M borane-tetrahydrofuran-complex in tetrahydrofurane were added and the reaction stirred under reflux for 30 min. 2 ml of 2 N aqueous hydrochloric acid were added, the reaction further stirred for 3 h under reflux, and the solvent removed under reduced pressure. Water adjusted to pH 9 with sodium hydroxide was added and the aqueous phase extracted three times with diethyl ether. The combined organic layers were dried over magnesium sulfate, filtered, and the solvent removed. The residue was purified via silica gel chromatography on chroma-bond column with cyclohexane/ethyl acetate 1:3 as eluent to yield 0.0155 g of the desired product

Workup

  1. temperatureunder reflux for 30 min
  2. customthe reaction
  3. stirringfurther stirred for 3 h
  4. temperatureunder reflux
  5. customthe solvent removed under reduced pressure
  6. additionwas added
  7. extractionthe aqueous phase extracted three times with diethyl ether
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent removed
  11. customThe residue was purified via silica gel chromatography on chroma-bond column with cyclohexane/ethyl acetate 1:3 as eluent

Sources & evidence

ORD record
ord-238c116c509c491ca6811cf1a72b622a
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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