Trifluoroacetic acid → HCID 67017828, compound

HRID 1015543Notes

Reaction equation

HRID 1015543 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]12[CH2:29][CH:17]3[CH2:18][C:19]([NH:21]C(=O)OC(C)(C)C)([CH2:20]1)[CH:15]([CH2:16]3)[CH2:14]2.FC(F)(F)C(O)=O>ClCCl>[NH2:21][C:19]12[CH2:18][CH:17]3[CH2:29][C:13]([CH2:12][N:3]4[C:2](=[O:1])[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[C:4]4=[O:11])([CH2:14][CH:15]1[CH2:16]3)[CH2:20]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86761371HCID 86761371, compound

Product 1

HCID 67017828HCID 67017828, compoundYield 120.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the compound obtained from step I (0.45 g, 1.12 mmol) in dichloromethane (1.1 mL) at 0° C. was added trifluoroacetic acid (1.1 mL). The reaction mixture was gradually warmed to room temperature and stirred for 1 h. The volatiles were removed under vacuum and the residue was triturated several times with diethyl ether to obtain 2-[(3-aminotricyclo[3.3.1.03,7]non-1-yl)methyl]-1H-isoindole-1,3(2H)-dione (0.4 g) as its trifluoroacetic acid salt in 86% yield. m/z (M+1) 297; 1H NMR (DMSO-d6) 300 MHz δ 8.05 (s (br), 2H), 7.92-7.80 (m, 4H), 3.51 (s, 2H), 2.38-2.30 (m, 1H), 2.30-2.22 (m, 1H), 1.85-1.66 (m, 6H), 1.60-1.50 (m, 3H), 1.45-1.38 (m, 1H).

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe residue was triturated several times with diethyl ether

Sources & evidence

ORD record
ord-b354505679b348a3b0e78798047c06dc
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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