Sulfuric Acid → HCID 59400175, compound

HRID 2389539Notes

Reaction equation

HRID 2389539 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][C@H:9]([NH:17]C(=O)[C@@H](O)C3C=CC=CC=3)[CH2:8]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O>C(O)C.CCOC(C)=O.[OH-].[Na+].O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][C@H:9]([NH2:17])[CH2:8]2)=[CH:28][CH:29]=1

Participants

7

Reactant 2

HCID 1118Sulfuric AcidHCID 59400150HCID 59400150, compound

Product 1

HCID 59400175HCID 59400175, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of (S)—N—((S)-1-(4-fluorobenzyl)-1,2,3,4-tetrahydroquinolin-3-yl)-2-hydroxy-2-phenylacetamide (350 mg, 0.90 mmol) in absolute ethanol (20 mL) was added concentrated sulfuric acid (2 mL). The reaction mixture was stirred at 85° C. for 24 hours. The mixture was diluted with EtOAc (100 mL), 6 M NaOH aqueous solution (20 mL) and water (50 mL). The phases were separated and the aqueous phase was extracted with EtOAc (100 mL). The combined organic phases were washed with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography using a gradient (0-10% MeOH in EtOAc). The desired product (S)-1-(4-fluorobenzyl)-1,2,3,4-tetrahydroquinolin-3-amine was obtained as yellow oil (169 mg, 73% yield). 1H NMR (DMSO-d6) 400 MHz δ 7.32-7.25 (m, 2H), 7.18-7.10 (m, 2H), 6.91-6.85 (m, 2H), 6.50-6.42 (m, 2H), 4.49 (d, J=16.8 Hz, 1H for AB system), 4.42 (d, J=16.8 Hz, 1H for AB system), 3.36-3.28 (m, 2H), 3.18-3.10 (m, 1H), 3.01 (dd, J=11.0, 8.6 Hz, 1H), 2.84 (dd, J=15.7, 2.7 Hz, 1H), 1.70 (br. s, 2H). LCMS m/e 258 (M+H).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with EtOAc (100 mL)
  3. washThe combined organic phases were washed with water (50 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-c8bb9e0ccee84a15ae2e79ebf89ca416
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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