Trifluoroacetic acid → 5-(7-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)-3,4-dihydro-2H-pyrrole

HRID 1054448Notes

Reaction equation

HRID 1054448 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([C:19]2[N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21][CH:20]=2)[C:12]2[O:17][CH2:16][CH2:15][O:14][C:13]=2[CH:18]=1>C(Cl)Cl.C(OCC)(=O)C>[F:8][C:9]1[CH:10]=[C:11]([C:19]2[CH2:20][CH2:21][CH2:22][N:23]=2)[C:12]2[O:17][CH2:16][CH2:15][O:14][C:13]=2[CH:18]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89618649tert-butyl 5-(7-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)-2,3-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 896184245-(7-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)-3,4-dihydro-2H-pyrroleYield 77.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

TFA (0.09 mL, 1.18 mmol) was added to a solution of tert-butyl 5-(7-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)-2,3-dihydro-1H-pyrrole-1-carboxylate (0.04 g, 0.117 mmol) in DCM (5 mL) at 0° C. and stirring was continued at 25° C. for 3 h. Reaction mixture was concentrated under reduced pressure to afford the crude, which was diluted with ethyl acetate, washed with saturated NaHCO3 solution, dried over anhydrous sodium sulphate to afford 5-(7-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)-3,4-dihydro-2H-pyrrole (Int-30) (0.02 g, 71% yield). MS (ESI): m/z 222 (M+H).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customto afford the crude, which
  4. washwashed with saturated NaHCO3 solution
  5. dry with materialdried over anhydrous sodium sulphate

Sources & evidence

ORD record
ord-53355187dd9a4b32b4e471ae8908fbeb
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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