Trifluoroacetic acid → ethyl 1-[(R)-2-amino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate

HRID 333446Notes

Reaction equation

HRID 333446 reaction equation
C(OC([NH:8][C@H:9]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[C:10]([N:12]1[CH2:17][CH2:16][C:15]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@H:9]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[C:10]([N:12]1[CH2:17][CH2:16][C:15]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66987792ethyl 1-[(R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate

Product 1

HCID 66987937ethyl 1-[(R)-2-amino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3.7 g (7.16 mmol) of ethyl 1-[(R)-2-tert-butoxycarbonylamino-3-(4-methoxy-phenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate dissolved in 30 mL of DCM immersed in a bath at 0° C. are added 10 mL of trifluoroacetic acid. After stirring for 1 hour 30 minutes, the solvents are evaporated off. The reaction medium is washed with aqueous 1N sodium hydroxide solution and extracted with DCM. The organic phase is then washed with water and then dried over MgSO4, filtered and concentrated. 2.74 g of ethyl 1-[(R)-2-amino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate in the form of a white powder are obtained in a yield of 92%.

Workup

  1. customimmersed in a bath at 0° C.
  2. customthe solvents are evaporated off
  3. washThe reaction medium is washed with aqueous 1N sodium hydroxide solution
  4. extractionextracted with DCM
  5. washThe organic phase is then washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8a42f4b582cf40b5869fb468bc301568
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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