Trifluoroacetic acid → 4-[5-Fluoro-1-(2-trimethylsilylethanesulfonyl)indol-3-yl]piperidine

HRID 609687Notes

Reaction equation

HRID 609687 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([F:23])[CH:21]=3)[N:16]([S:24]([CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])(=[O:26])=[O:25])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[N:16]([S:24]([CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])(=[O:26])=[O:25])[CH:15]=[C:14]2[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22615698N-tert-butoxycarbonyl-4-[5-fluoro-1-(2-trimethylsilylethanesulfonyl)indol-3-yl]piperidine

Product 1

HCID 226157204-[5-Fluoro-1-(2-trimethylsilylethanesulfonyl)indol-3-yl]piperidineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butoxycarbonyl-4-[5-fluoro-1-(2-trimethylsilylethanesulfonyl)indol-3-yl]piperidine (1.33 g, 2.73 mmol), [prepared as described in Step 2, above] in methylene chloride (3 ml), was added trifluoroacetic acid (4 ml). After 2 h, the reaction mixture was concentrated in vacuo and the residue was partitioned between methylene chloride (50 ml) and of 1M NaOH (10 ml). The organic layers were dried over MgSO4 and concentrated in vacuo to afford 4-[5-fluoro-1-(2-trimethylsilylethanesulfonyl)indol-3-yl]piperidine (100%). This material was used in the next step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between methylene chloride (50 ml) and of 1M NaOH (10 ml)
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0dc7ee64140f453992f6f26d2754f44e
Source dataset
uspto-grants-1999_12
Patent number
US05998412

Reaction notes

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