Trifluoroacetic acid → 1-((2S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-2-yl)ethanamine

HRID 556168Notes

Reaction equation

HRID 556168 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C@@H:11]([CH:19]([NH:21]C(=O)OC(C)(C)C)[CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C@@H:11]([CH:19]([NH2:21])[CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58950748tert-butyl 1-((2S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-2-yl)ethylcarbamate

Product 1

HCID 589507421-((2S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-2-yl)ethanamineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the above tert-butyl 1-((2S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-2-yl)ethylcarbamate 50b (50 mg, 0.12 mmol) in CH2Cl2 (3 mL) was added TFA (2 mL). The reaction mixture was stirred for 1 h before being concentrated. The residue was subjected to reverse phase column chromatography (CH3CN/H2O/0.1% formic acid=5% to 100%) to give 51 (34 mg, 90%). 1HNMR (400 MHz, CDCl3) δ 7.36 (d, J=8.0 Hz, 1 H), 7.26 (d, J=2.0 Hz, 1 H), 7.12 (m, 2 H), 7.03 (m, 1 H), 7.00 (dd, J=1.6, 8.0 Hz, 1 H), 6.71 (d, J=8.0 Hz, 1 H), 4.04 (dd, J=5.2, 12.0 Hz, 1 H), 2.92 (m, 2 H), 2.72 (dd, J=12.4, 16.0 Hz, 1 H), 2.22 (m, 2 H), 1.85 (m, 1 H), 1.48 (q, J=12.0 Hz, 1H), 1.20 (d, J=6.0 Hz, 3 H); 13CNMR (100 MHz, CDCl3) δ 147.45, 138.65, 136.88, 132.65, 130.87, 130.69, 130.46, 129.54, 129.43, 128.43, 126.02, 126.26, 77.45, 51.35, 40.70, 41.77, 37.10, 32.94, 20.25; ESI MS m/z 320.0.

Workup

  1. concentrationbefore being concentrated

Sources & evidence

ORD record
ord-796dce7d6caa44bc8928d9a3b85a4ca7
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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