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

HRID 366485Notes

Reaction equation

HRID 366485 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-trimethylsilylethane-sulfonyl)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-1461e1dbb09348a7a52b5247136f68f1
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Reaction notes

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