Trifluoroacetic acid → (R)-3-amino-4-[4-(4-fluorophenoxy)-piperidin-1-yl]-butyric acid benzyl ester

HRID 1797263Notes

Reaction equation

HRID 1797263 reaction equation
[CH2:1]([O:8][C:9](=[O:35])[CH2:10][C@@H:11]([NH:27]C(OC(C)(C)C)=O)[CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:35])[CH2:10][C@@H:11]([NH2:27])[CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([O:19][C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[CH2:17][CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68576098(R)-3-tert-butoxycarbonylamino-4-[4-(4-fluoro-phenoxy)-piperidin-1-yl]butyric acid benzyl ester

Product 1

HCID 68576481(R)-3-amino-4-[4-(4-fluorophenoxy)-piperidin-1-yl]-butyric acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-3-tert-butoxycarbonylamino-4-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-butyric acid benzyl ester (0.488 g, 1.0 mmol) in DCM (8 ml) is treated with trifluoroacetic acid (2 ml). The reaction mixture is stirred at ambient temperature for 1 hour. The solvent is evaporated and the residue taken up in DCM and washed with saturated aqueous NaHCO3. The organic phase is dried over MgSO4 and evaporated to yield (R)-3-amino-4-[4-(4-fluorophenoxy)-piperidin-1-yl]-butyric acid benzyl ester. [MH]+ 387.1

Workup

  1. customThe solvent is evaporated
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialThe organic phase is dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-5c4e12ecc1c7492084993ba09c04b88f
Source dataset
uspto-grants-2006_04
Patent number
US07034042B2

Reaction notes

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