Water → HCID 67422631, compound

HRID 880725Notes

Reaction equation

HRID 880725 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[C:25]([F:27])[C:24]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:23][C:22]=2[O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.O>ClCCl>[CH2:37]([O:36][C:22]1[CH:23]=[C:24]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:25]([F:27])=[CH:26][C:21]=1[CH:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 67421015HCID 67421015, compound

Product 1

HCID 67422631HCID 67422631, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

280 μl (3.7 mmol, 10 eq) of trifluoroacetic acid are added to a solution of 184 mg (0.37 mmol, 1 eq) of 4-(2,4-bis(benzyloxy)-5-fluorophenyl)piperidine-1-carboxylic acid tert-butyl ester in 3 ml of dichloromethane. The reaction medium is stirred at ambient temperature for 1 hour. The reaction medium is treated with 10 ml of water and then extracted with dichloromethane. The organic phases are combined, washed with a saturated solution of sodium hydrogen carbonate and then with a saturated solution of sodium chloride, dried over magnesium sulphate and evaporated. 150 mg of 4-(2,4-bis(benzyloxy)-5-fluorophenyl)piperidine are obtained. Yield=100%.

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with a saturated solution of sodium hydrogen carbonate
  3. dry with materialwith a saturated solution of sodium chloride, dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-a65859ef122b4f46a3b79334f6609927
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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