Water → HCID 86626022, compound

HRID 870367Notes

Reaction equation

HRID 870367 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].FC(F)(F)C1C=CC(S(NC2C=CC3C[C@@H]4[C@H](CCCN4C(=O)CC)CC=3C=2)(=O)=O)=CC=1.[F:39][C:40]([F:70])([F:69])[C:41]1[CH:46]=[CH:45][C:44]([S:47]([NH:50][C:51]2[CH:68]=[CH:67][C:54]3[CH2:55][C@@H:56]4[C@@H:61]([CH2:62][C:53]=3[CH:52]=2)[N:60]([C:63](=O)[CH2:64][CH3:65])[CH2:59][CH2:58][CH2:57]4)(=[O:49])=[O:48])=[CH:43][CH:42]=1.O>O1CCCC1>[F:70][C:40]([F:39])([F:69])[C:41]1[CH:42]=[CH:43][C:44]([S:47]([NH:50][C:51]2[CH:68]=[CH:67][C:54]3[CH2:55][C@@H:56]4[C@@H:61]([CH2:62][C:53]=3[CH:52]=2)[N:60]([CH2:63][CH2:64][CH3:65])[CH2:59][CH2:58][CH2:57]4)(=[O:48])=[O:49])=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86626020HCID 86626020, compoundHCID 86626023HCID 86626023, compound

Product 1

HCID 86626022HCID 86626022, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

To a suspension of 0.035 g of lithium aluminium hydride (0.922 mmol) in 2.5 ml tetrahydrofurane were added at 4° C. a solution of 0.2 g of the 1:1 mixture of trans-4-trifluoromethyl-N-(1-propionyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinolin-7-yl)benzenesulfonamide and trans-4-trifluoromethyl-N-(1-propionyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinolin-8-yl)-benzenesulfonamide (0.429 mmol) in 2.5 ml tetra-hydrofuran. After stirring for 5 minutes at 10° C., 1 mL water was cautiously added, the solvent evaporated and the residue treated with diethyl ether and water. The aqueous phase was reextracted with diethylether, and the combined organic layers dried over magnesium sulfate, filtered and the solvent evaporated under reduced pressure. The crude product was purified via preparative HPLC (compression column, Delta Pack 40 mm diameter) using a gradient consisting of methanol/water/0.1% acetic as eluent; fraction 3, m=31.9 mg (8-isomer), fraction. 4, m=22.4 mg, fractions. 5-7, m=22.5 mg (7-isomer),

Workup

  1. additionwere added at 4° C.
  2. customthe solvent evaporated
  3. additionthe residue treated with diethyl ether and water
  4. dry with materialthe combined organic layers dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified via preparative HPLC (compression column, Delta Pack 40 mm diameter)

Sources & evidence

ORD record
ord-259318bb37124c92ae44638ddd1b816f
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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