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

HRID 556170Notes

Reaction equation

HRID 556170 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]([C@@H: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 66809048(S)-1-((2S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-2-yl)ethanamineYield 106.4%

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 50a (40 mg, 0.096 mmol) in CH2Cl2 (2 mL) was added TFA (2 mL). The reaction mixture was stirred for 1 h before being concentrated. The residue was subjected reverse phase column chromatography (CH3CN/H2O/0.1% Formic acid=5% to 100%) to give 52 (32.7 mg, 86%). 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=8.0 Hz, 1 H), 7.27 (d, J=2.0 Hz, 1 H), 7.15 (m, 2 H), 7.02 (m, 2 H), 6.72 (d, J=7.6 Hz, 1 H), 4.04 (dd, J=5.2, 12.0 Hz, 1 H), 2.95 (m, 2 H), 2.78 (dd, J=12.0, 15.6 Hz, 1 H), 2.13 (m, 1 H), 1.80 (m, 1 H), 1.51 (q, J=12.4 Hz, 1 H), 1.35 (broad, 1 H), 1.14 (d, J=6.4 Hz, 3 H); 13CNMR (100 MHz, CDCl3) δ 147.67, 138.79, 137.29, 132.64, 130.88, 130.68, 130.41, 129.57, 129.43, 128.43, 126.58, 126.15, 51.16, 46.91, 42.31, 37.48, 32.60, 21.20; ESI MS m/z 320.1.

Workup

  1. concentrationbefore being concentrated

Sources & evidence

ORD record
ord-08c5081425fd40b5a42abd67be8aaa33
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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