Hydrochloric Acid → HCID 69413704, compound

HRID 1766397Notes

Reaction equation

HRID 1766397 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:12]2[CH2:21][CH2:20][CH:19]3[CH:14]([CH:15]([C:22]([O:24]CC)=[O:23])[CH2:16][CH2:17][CH2:18]3)[CH2:13]2)=[O:11])=[CH:4][CH:3]=1.[OH-].[K+].Cl>O1CCCC1.O.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([N:12]2[CH2:21][CH2:20][CH:19]3[CH:14]([CH:15]([C:22]([OH:24])=[O:23])[CH2:16][CH2:17][CH2:18]3)[CH2:13]2)=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2×HCID 86600514HCID 86600514, compound

Product 1

HCID 69413704HCID 69413704, compoundYield 98.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl (4aSR,8SR,8aSR)-2-[3-(4-fluorophenyl)propanoyl]decahydroisoquinoline-8-carboxylate (385 mg, 1.07 mmol) in tetrahydrofuran (5 mL) was added to a solution of potassium hydroxide (168 mg, 3.0 mmol) in water (5 mL). The resulting solution was stirred at room temperature for 16 hours. Additional potassium hydroxide (385 mg, 1.07 mmol) dissolved in methanol (5 mL) was added, and stirring was continued for an additional 5 hours. The mixture was treated with concentrated aqueous hydrochloric acid until the pH was about 1. The mixture was concentrated to a volume of about 5 mL and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated to provide a white solid (350 mg, 98%). 1H NMR (300 MHz, CDCl3) δ7.11 (m, 2H), 6.90 (m, 2H), 4.66 (m, 1H), 3.80 (m, 1H), 2.85 (m, 2H), 2.7-2.4 (m, 3H), 2.1-1.9 (m, 2H), 1.80 (m, 1H), 1.7-0.9 (m, 9H). Mass spec (ES+) m/z 334.2 (M+H+, 100%).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for an additional 5 hours
  4. concentrationThe mixture was concentrated to a volume of about 5 mL
  5. extractionextracted three times with ethyl acetate
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c9661ecc48444fdca38d3c3f83af2c5d
Source dataset
uspto-grants-2007_06
Patent number
US07230022B2

Reaction notes

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