Trifluoroacetic acid → ethyl 1-[(2R)-2-amino-2-phenylethyl]piperidine-4-carboxylate

HRID 64413Notes

Reaction equation

HRID 64413 reaction equation
C(OC([NH:8][C@H:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C@H:9]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86713423ethyl 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl}piperidine-4-carboxylate

Product 1

HCID 86713422ethyl 1-[(2R)-2-amino-2-phenylethyl]piperidine-4-carboxylateYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 160 mg of ethyl 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl}piperidine-4-carboxylate in 1.5 mL of dichloromethane was added 0.7 mL of trifluoroacetic acid, followed by stirring for 1 hour. The solvent was evaporated under reduced pressure, and a saturated aqueous sodium carbonate solution and a chloroform-methanol mixed solution were added thereto in this order to carry out a layer separation operation. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to obtain 120 mg of ethyl 1-[(2R)-2-amino-2-phenylethyl]piperidine-4-carboxylate.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additiona saturated aqueous sodium carbonate solution and a chloroform-methanol mixed solution were added
  3. customa layer separation operation
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b23b9a5ade5d484686cc78efe268cc66
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

Loading…