Trifluoroacetic acid → HCID 10158467, compound

HRID 1883609Notes

Reaction equation

HRID 1883609 reaction equation
[CH2:1]([C:8]1[C:13]2[O:14][CH:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH:16]3[C:12]=2[CH:11]=[C:10]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([C:8]1[C:13]2[O:14][CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH:16]3[C:12]=2[CH:11]=[C:10]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 23508107HCID 23508107, compound

Product 1

HCID 10158467HCID 10158467, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 6-benzyl-8-(2,4-dichlorophenyl)-3,4,4a,9b-tetrahydro[1]benzofuro[3,2-c]pyridine-2(1H)-carboxylate (0.137 g, 0.270 mmol) was dissolved in CH2Cl2 (5 mL). Trifluoracetic acid (0.44 mL, 5.670 mmol) was added and the reaction mixture was stirred at rt under N2 for 4 h. The reaction mixture was cooled to 0° C. and 25% aqueous NaOH (15 mL) was added. The reaction mixture was partitioned between CH2Cl2 and water. The water layer was extracted with CH2Cl2 (2×). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography (1% NH4OH, 5.95% CH3OH, 93.05% CH2Cl2), and Example 250 was obtained in 86% yield. MS (ESI+) for C24H21Cl2NO m/z 410.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customThe reaction mixture was partitioned between CH2Cl2 and water
  3. extractionThe water layer was extracted with CH2Cl2 (2×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by chromatography (1% NH4OH, 5.95% CH3OH, 93.05% CH2Cl2)
  8. customExample 250 was obtained in 86% yield

Sources & evidence

ORD record
ord-a2c626b3d5134e968f6d15b31ab66ddd
Source dataset
uspto-grants-2004_07
Patent number
US06762191B2

Reaction notes

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