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

HRID 556166Notes

Reaction equation

HRID 556166 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 86.4%

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 49a (Example 21.3) (100 mg, 0.24 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 to reverse phase column chromatography (CH3CN/H2O/0.1% formic acid=5% to 100%) to give 46 (66 mg, 86%). 1HNMR (400 MHz, CDCl3) δ 7.34 (d, J=8.4 Hz, 1 H), 7.26 (d, J=2.0 Hz, 1 H), 7.20 (m, 1 H), 7.16-7.08 (m, 2 H), 7.01 (dd, J=1.6, 8.0 Hz, 1H), 6.80 (d, J=7.2 Hz, 1H), 6.46 (s, 1H), 4.09 (t, J=7.6 Hz, 1H), 3.59 (q, J=6.0 Hz, 1 H), 2.60 (dd, J=6.8, 16.4 Hz, 1 H), 2.53 (dd, J=8.4, 16.4 Hz, 1 H), 1.38 (broad, 2 H), 1.14 (d, J=6.8 Hz, 3 H); 13CNMR (100 MHz, CDCl3) δ 144.81, 144.36, 136.15, 134.67, 132.51, 130.52, 130.41, 127.98, 127.77, 127.60, 127.34, 126.70, 120.93, 120.90, 51.91, 43.77, 32.86, 22.11; ESI MS m/z 318.0.

Workup

  1. concentrationbefore being concentrated

Sources & evidence

ORD record
ord-61dbe27df93b40fea078e4edbd2736bf
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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