Trifluoroacetic acid → HCID 68898419, compound

HRID 7191Notes

Reaction equation

HRID 7191 reaction equation
[C:1]1([NH:7][C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]2[NH:14]C(OC(C)(C)C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]1([NH:7][C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]2[NH2:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86587219cis-N-phenyl-N'-(t-butyloxycarbonyl)-cyclohexane-1,2-diamine

Product 1

HCID 68898419HCID 68898419, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The cis-N-phenyl-N′-(t-butyloxycarbonyl)-cyclohexane-1,2-diamine isomer from above (0.095 g, 0.33 mmol) was dissolved in CH2Cl2 (2 mL) and treated with trifluoroacetic acid (2 mL) and the mixture stirred overnight. The reaction was worked up to afford the title compound (0.069 g) as a pale yellow solid. 1H NMR (CDCl3) 1.28–1.37 (m, 5H), 1.50–1.63 (m, 6H), 3.18 (br s, 1H), 3.42–3.45 (m, 1H), 6.63–6.70 (m, 3H), 7.16 (br t, 2H, J=7.5 Hz).

Sources & evidence

ORD record
ord-77c7461546cf4e08b92e4d0aa416cd1b
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Reaction notes

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