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

HRID 556165Notes

Reaction equation

HRID 556165 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10]1[CH2:19][C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:27][C:22]1[CH:21]=[C:20]([C@H:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]([CH:8]([NH2:7])[CH3:9])[CH2:19]2)[CH:25]=[CH:24][C:23]=1[Cl:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66808903tert-butyl-1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethylcarbamate

Product 1

HCID 589507391-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethanamineYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl-1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethylcarbamate 49b (100 mg, 0.24 mmol) in CH2Cl2 (5 mL) was added TFA (5 mL). The reaction mixture was stirred for 2 h before being concentrated. The residue was subjected reverse phase column chromatography (CH3CN/H2O/0.1% Formic acid=5% to 100%) to give 1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethanamine 45 (65 mg, 85%). 1H NMR (400 MHz, CDCl3) δ 7.33 (d, J=8.0 Hz, 1 H), 7.23 (d, J=2.4 Hz, 1 H), 7.19 (d, J=7.2 Hz, 1 H), 7.14-7.08 (m, 2 H), 6.98 (dd, J=2.4, 8.4 Hz, 1H), 6.82 (d, J=7.2 Hz, 1 H), 6.46 (s, 1 H), 4.08 (t, J=8.4 Hz, 1 H), 3.61 (q, J=6.4 Hz, 1 H), 2.69 (dd, J=7.6, 16.8 Hz, 1 H), 2.46 (dd, J=8.8, 16.8 Hz, 1 H), 2.10 (broad, 2 H), 1.14 (d, J=8.0 Hz, 3 H); 13C NMR (100 MHz, CDCl3) δ 144.75, 143.04, 136.16, 134.41, 132.52, 130.53, 130.41, 127.96, 127.80, 127.62, 127.52, 126.80, 121.07, 52.17, 43.68, 32.41, 21.53; ESI MS m/z 318.0.

Workup

  1. concentrationbefore being concentrated

Sources & evidence

ORD record
ord-a115553f14a64b5a8e653b8baf0f21eb
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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