Trifluoroacetic acid → 3-(8-Aza-bicyclo[3.2.1]oct-2-en-3-yl)-1H-indole

HRID 987567Notes

Reaction equation

C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([Si](C(C)(C)C)(C)C)[CH:18]=1)(O)[CH2:12]2)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:9]12[NH:8][CH:13]([CH2:14][CH2:15]1)[CH2:12][C:11]([C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=1)=[CH:10]2

Participants

Conditions

Temperature: 23 °C

Procedure

To 1.25 g (2.74 mmol) tert-butyl-3-{1-[tert-butyl(dimethyl)silyl]-1H-indol-3-yl}-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate in 25 mL CH2Cl2 is added 6 mL of TFA. After stirring at 23° C. for 45 min, the reaction mixture is poured into sat. aqueous NaHCO3 (300 mL) and extracted with 3×50 mL CH2Cl2. The combined organics are washed with 1×100 mL H2O, 1×100 mL of brine, dried over Na2SO4, filtered and evaporated to give 603 mg (2.24 mmol, an 82% yield) of the title compound as a yellow/orange oil. MS (ES) m/z 269 (MH)+.

Workup

extractionextracted with 3×50 mL CH2Cl2
washThe combined organics are washed with 1×100 mL H2O, 1×100 mL of brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customto give 603 mg (2.24 mmol

Sources & evidence

ORD record: ord-8b9d5a191ba64f2c92727b15acfbacaf
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632824B2

Reaction notes

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