Trifluoroacetic acid → HCID 59346313, compound

HRID 733100Notes

Reaction equation

HRID 733100 reaction equation
C(OC([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][CH2:11]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67232240HCID 67232240, compound

Product 1

HCID 59346313HCID 59346313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 3-(4-{[(tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)propanoate (500 mg, 1.6 mmol, step 1 of Example 10) in CH2Cl2 (5 mL), trifluoroacetic acid (1.2 mL, 16 mmol) was added and stirred overnight at room temperature. The mixture was concentrated, and the residual oil was dissolved in CH2Cl2 (60 mL) and solid K2CO3 (5 g) was added, and stirred for 10 min. The mixture was filtered, and the filtrate was concentrated to give ethyl 3-[4-(aminomethyl)piperidin-1-yl]propanoate as a pale yellow oil. Following coupling reaction was carried out according to the procedure described in step 6 of Example 1 from 3,3-dimethyl-1,3-dihydro-2H-indol-2-one (Robertson, David W et al., J. Med. Chem., 1986, 29, 1832) and ethyl 3-[4-(aminomethyl)piperidin-1-yl]propanoate.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residual oil was dissolved in CH2Cl2 (60 mL)
  3. additionsolid K2CO3 (5 g) was added
  4. stirringstirred for 10 min
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d967847f96ab4c43a7eac9023c8627d8
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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