Trifluoroacetic acid → HCID 22458544, compound

HRID 2185477Notes

Reaction equation

HRID 2185477 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[CH2:29]([O:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)=[CH:23][CH:24]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22458519Tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylate

Product 1

HCID 22458544HCID 22458544, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (6 mL) was added to a solution of N-tert-butoxycarbonyl-4-(4-benzyloxyphenoxy)piperidine (B, 473 mg) in dichloromethane (12 mL) at room temperature. After stirring at room temperature for 20 hr, the reaction was quenched with saturated sodium hydrogen carbonate. The resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the titled compound (345 mg) as a yellow brown solid, which was used in the next reaction without further purification.

Workup

  1. customthe reaction was quenched with saturated sodium hydrogen carbonate
  2. extractionThe resulting mixture was extracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0b776c03f5549e2b1f3ad7222ff538d
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…