Hydrochloric Acid → HCID 89709503, compound

HRID 717901Notes

Reaction equation

HRID 717901 reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[NH:12][CH:11]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:10]3[CH2:22][CH2:23][CH2:24][O:25][CH:9]3[C:8]=2[CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>>[CH:16]1([CH:11]2[CH:10]3[CH2:22][CH2:23][CH2:24][O:25][CH:9]3[C:8]3[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:15]=[CH:14][C:13]=3[NH:12]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131734163HCID 131734163, compound

Product 1

HCID 89709503HCID 89709503, compoundYield 69.1%

Conditions

Temperature
65 °C

Procedure

To (4aSR*,5SR*,10bSR*)-ethyl-5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline-9-carboxylate (Base of example 10, obtained according to example 1 procedure) (145 mg, 0.422 mmol) was added a 0.5 NaOH solution (6 mL, in MeOH/H2O 1:1) and the reaction mixture heated at 65° C. for 24 h. After cooling back to r.t., the reaction mixture was neutralized with 10% HCl solution. The product was extracted with AcOEt twice. The combined organic fractions were dried over Na2SO4 and the solvent removed under reduced pressure after filtration to afford (4aSR*,5SR*,10bSR*)-5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline-9-carboxylic acid (92 mg, 69%).

Workup

  1. temperatureAfter cooling back to r.t.
  2. extractionThe product was extracted with AcOEt twice
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. customthe solvent removed under reduced pressure
  5. filtrationafter filtration

Sources & evidence

ORD record
ord-1ccdbf757bea49b48777209b6620f6ec
Source dataset
uspto-grants-2015_11
Patent number
US09193738B2

Reaction notes

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