Trifluoroacetic acid → HCID 23508101, compound

HRID 1883605Notes

Reaction equation

HRID 1883605 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:12]2[O:21][CH:20]3[CH:15]([CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][CH2:19]3)[C:13]=2[CH:14]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:12]2[O:21][CH:20]3[CH:15]([CH:16]=[N:17][CH2:18][CH2:19]3)[C:13]=2[CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 12125451HCID 12125451, compound

Product 1

HCID 23508101HCID 23508101, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 8-(2,4-dichlorophenyl)-3,4,4a,9b-tetrahydro[1]benzofuro[3,2-c]pyridine-2(1H)-carboxylate (0.221 g, 0.53 mmol) was dissolved in CH2Cl2 (7 mL). Trifluoracetic acid (0.81 mL, 20 equiv.) was added, and the reaction mixture was stirred at rt under N2 for 2 h. The reaction mixture was cooled to −5° C. and 2N aqueous NaOH (8 mL) was added. The reaction mixture was partitioned between CH2Cl2 and water. The water layer was extracted with CH2Cl2 (2×) and with 25:1 CH2Cl2:CH3OH (2×). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to provide the title compound (0.16 g, 98%). MS (ESI+) for C17H15Cl2NO m/z 320.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to −5° C.
  2. customThe reaction mixture was partitioned between CH2Cl2 and water
  3. extractionThe water layer was extracted with CH2Cl2 (2×) and with 25:1 CH2Cl2
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d2270ae081144a3ab0b2e82b34225c5
Source dataset
uspto-grants-2004_07
Patent number
US06762191B2

Reaction notes

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