Trifluoroacetic acid → HCID 19599733, compound

HRID 609657Notes

Reaction equation

HRID 609657 reaction equation
[C:1]1([CH:7]([N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][C:10]2=[O:22])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]1([CH:7]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][C:10]2=[O:22])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19599742HCID 19599742, compound

Product 1

HCID 19599733HCID 19599733, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared in the same manner as that described in Example 5, Step 2, using 1-(1-phenylethyl)-4-(tert-butyloxycarbonyl)piperazin-2-one (673 mg, 2.2 mmol), trifluoroacetic acid (4 mL) and CH2Cl2 (40 mL). The crude product was chromatographed on silica gel, eluting with CH2Cl2 :MeOH (90:10), to afford the amine (307 mg, 68%) as a colourless oil. 1H NMR (250 MHz, CDCl3) δ1.53 (3H, d, J=7.2 Hz), 2.75-2.94 (2H, m), 2.98-3.07 (1H, m), 3.12-3.21 (1H, m), 3.62 (2H, s), 6.13 (1H, q, J=7.2 Hz), 7.24-7.39 (5H, m).

Workup

  1. customPrepared in the same manner as
  2. customThe crude product was chromatographed on silica gel
  3. washeluting with CH2Cl2 :MeOH (90:10)

Sources & evidence

ORD record
ord-917abd0e89f946129d38a0f212983a5a
Source dataset
uspto-grants-1999_12
Patent number
US05998415

Reaction notes

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